diff --git a/src/main/java/org/shanerx/tradeshop/data/config/ConfigManager.java b/src/main/java/org/shanerx/tradeshop/data/config/ConfigManager.java
index b8241e72..44537f60 100644
--- a/src/main/java/org/shanerx/tradeshop/data/config/ConfigManager.java
+++ b/src/main/java/org/shanerx/tradeshop/data/config/ConfigManager.java
@@ -29,6 +29,7 @@
 import com.google.common.base.Charsets;
 import com.google.common.io.Files;
 import org.apache.commons.lang.Validate;
+import org.bukkit.Bukkit;
 import org.bukkit.ChatColor;
 import org.bukkit.configuration.file.FileConfiguration;
 import org.bukkit.configuration.file.YamlConfiguration;
@@ -41,8 +42,10 @@
 import java.io.Writer;
 import java.util.Arrays;
 import java.util.Comparator;
+import java.util.HashSet;
 import java.util.LinkedHashMap;
 import java.util.Map;
+import java.util.Set;
 import java.util.logging.Level;
 
 public class ConfigManager {
@@ -78,7 +81,7 @@ public String colour(String toColour) {
         return ChatColor.translateAlternateColorCodes('&', toColour);
     }
 
-    public void load() {
+    public boolean load() {
         try {
             if (!PLUGIN.getDataFolder().isDirectory()) {
                 PLUGIN.getDataFolder().mkdirs();
@@ -93,23 +96,24 @@ public void load() {
 
         config = YamlConfiguration.loadConfiguration(file);
 
-        setDefaults();
+        return setDefaults();
     }
 
     public void reload() {
-        load();
+        Set<Boolean> hasUpgraded = new HashSet<>();
+        hasUpgraded.add(load());
 
         switch (configType) {
             case CONFIG:
-                Setting.upgrade();
+                hasUpgraded.add(Setting.upgrade());
                 PLUGIN.setUseInternalPerms(Setting.USE_INTERNAL_PERMISSIONS.getBoolean());
                 break;
             case MESSAGES:
-                Message.upgrade();
+                hasUpgraded.add(Message.upgrade());
                 break;
         }
 
-        save();
+        save(hasUpgraded.contains(true));
 
         PLUGIN.setSkipHopperProtection(
                 Setting.BITRADESHOP_HOPPER_EXPORT.getBoolean() &&
@@ -118,15 +122,28 @@ public void reload() {
                         Setting.TRADESHOP_HOPPER_EXPORT.getBoolean());
     }
 
-    public void setDefaults() {
+    public boolean setDefaults() {
+        Set<Boolean> hasUpgraded = new HashSet<>();
+
         switch (configType) {
             case CONFIG:
-                Arrays.stream(Setting.values()).forEach((setting) -> addKeyValue(setting.getPath(), setting.getDefaultValue()));
+                Arrays.stream(Setting.values()).forEach((setting) -> hasUpgraded.add(addKeyValue(setting.getPath(), setting.getDefaultValue())));
                 break;
             case MESSAGES:
-                Arrays.stream(Message.values()).forEach((message) -> addKeyValue(message.getPath(), message.getDefaultValue()));
+                Arrays.stream(Message.values()).forEach((message) -> hasUpgraded.add(addKeyValue(message.getPath(), message.getDefaultValue())));
                 break;
         }
+
+        return hasUpgraded.contains(true);
+    }
+
+    /**
+     * Saves the file if passed boolean is true
+     *
+     * @param shouldSave true if save should proceed
+     */
+    public void save(boolean shouldSave) {
+        if (shouldSave) save();
     }
 
     public void save() {
@@ -181,17 +198,22 @@ public void save() {
         config = YamlConfiguration.loadConfiguration(file);
     }
 
-    private void addKeyValue(String node, Object value) {
+    private boolean addKeyValue(String node, Object value) {
         if (value instanceof Map) {
             for (Map.Entry entry : ((Map<?, ?>) value).entrySet()) {
                 String newNode = node + "." + entry.getKey().toString();
                 if (config.get(newNode) == null || (config.get(newNode) != null && config.get(newNode).toString().isEmpty())) {
+                    Bukkit.getLogger().log(Level.WARNING, "TS reload issue ->\n" + newNode + " = " + config.get(newNode).toString() + " | " + entry.getValue().toString());
                     config.set(newNode, entry.getValue().toString());
+                    return true;
                 }
             }
         } else if (config.get(node) == null || (config.get(node) != null && config.get(node).toString().isEmpty())) {
             config.set(node, value);
+            return true;
         }
+
+        return false;
     }
 
     public enum ConfigType {
diff --git a/src/main/java/org/shanerx/tradeshop/data/config/Message.java b/src/main/java/org/shanerx/tradeshop/data/config/Message.java
index 8028966a..f2de16e1 100644
--- a/src/main/java/org/shanerx/tradeshop/data/config/Message.java
+++ b/src/main/java/org/shanerx/tradeshop/data/config/Message.java
@@ -37,9 +37,11 @@
 import org.yaml.snakeyaml.Yaml;
 
 import java.util.Arrays;
+import java.util.HashSet;
 import java.util.List;
 import java.util.Map;
 import java.util.Objects;
+import java.util.Set;
 import java.util.regex.Matcher;
 import java.util.regex.Pattern;
 
@@ -117,13 +119,15 @@ public enum Message {
     }
 
     // Method to fix any values that have changed with updates
-    static void upgrade() {
+    static boolean upgrade() {
         double version = MESSAGE_VERSION.getDouble();
+        Set<Boolean> hasUpgraded = new HashSet<>(); // Uses this instead of a boolean to later replace below ifs with boolean return methods...
 
         //Changes if CONFIG_VERSION is below 1.1, then update to 1.1
         if (checkVersion(version, 1.1)) {
             if (TOO_MANY_ITEMS.getString().equals("&cThis trade can not take any more %side%!")) {
                 TOO_MANY_ITEMS.setValue(PLUGIN.getLanguage().getDefault(Language.LangSection.MESSAGE, TOO_MANY_ITEMS.getPath()));
+                hasUpgraded.add(true);
             }
             version = 1.1;
         }
@@ -133,8 +137,10 @@ static void upgrade() {
             Arrays.stream(values()).forEach((message) -> {
                 String str = message.getString().replace("{", "%").replace("}", "%");
 
-                if (!str.equals(message.getString()))
+                if (!str.equals(message.getString())) {
                     message.setValue(str);
+                    hasUpgraded.add(true);
+                }
 
             });
             version = 1.2;
@@ -144,12 +150,15 @@ static void upgrade() {
         if (checkVersion(version, 1.3)) {
             if (INSUFFICIENT_ITEMS.getString().equals("&cYou do not have &e%AMOUNT% %ITEM%&c!")) {
                 INSUFFICIENT_ITEMS.setValue(PLUGIN.getLanguage().getDefault(Language.LangSection.MESSAGE, INSUFFICIENT_ITEMS.getPath()));
+                hasUpgraded.add(true);
             }
             if (SHOP_INSUFFICIENT_ITEMS.getString().equals("&cThis shop does not have enough &e%AMOUNT% %ITEM%&c to trade!")) {
                 SHOP_INSUFFICIENT_ITEMS.setValue(PLUGIN.getLanguage().getDefault(Language.LangSection.MESSAGE, SHOP_INSUFFICIENT_ITEMS.getPath()));
+                hasUpgraded.add(true);
             }
             if (ON_TRADE.getString().equals("&aYou have traded your &e%AMOUNT2% %ITEM2% &afor &e%AMOUNT1% %ITEM1% &awith %SELLER%")) {
                 ON_TRADE.setValue(PLUGIN.getLanguage().getDefault(Language.LangSection.MESSAGE, ON_TRADE.getPath()));
+                hasUpgraded.add(true);
             }
 
 
@@ -157,6 +166,8 @@ static void upgrade() {
         }
 
         MESSAGE_VERSION.setValue(version != 0.0 ? version : 1.3);
+
+        return hasUpgraded.contains(true);
     }
 
     private static boolean checkVersion(double version, double maxVersion) {
diff --git a/src/main/java/org/shanerx/tradeshop/data/config/Setting.java b/src/main/java/org/shanerx/tradeshop/data/config/Setting.java
index 79e24074..9a4f6a53 100644
--- a/src/main/java/org/shanerx/tradeshop/data/config/Setting.java
+++ b/src/main/java/org/shanerx/tradeshop/data/config/Setting.java
@@ -32,8 +32,10 @@
 import org.yaml.snakeyaml.Yaml;
 
 import java.util.Arrays;
+import java.util.HashSet;
 import java.util.List;
 import java.util.Map;
+import java.util.Set;
 
 public enum Setting {
 
@@ -170,8 +172,9 @@ public static Setting findSetting(String search) {
     }
 
     // Method to fix any values that have changed with updates
-    static void upgrade() {
+    static boolean upgrade() {
         double version = CONFIG_VERSION.getDouble();
+        Set<Boolean> hasUpgraded = new HashSet<>(); // Uses this instead of a boolean to later replace below ifs with boolean return methods...
         ConfigManager configManager = PLUGIN.getSettingManager();
 
         // 2.2.2 Changed enable debug from true/false to integer
@@ -184,46 +187,55 @@ static void upgrade() {
             if (configManager.getConfig().contains("itradeshop.owner")) {
                 configManager.getConfig().set(ITRADESHOP_OWNER.path, configManager.getConfig().get("itradeshop.owner"));
                 configManager.getConfig().set("itradeshop.owner", null);
+                hasUpgraded.add(true);
             }
 
             if (configManager.getConfig().contains("itradeshop.header")) {
                 configManager.getConfig().set(ITRADESHOP_HEADER.path, configManager.getConfig().get("itradeshop.header"));
                 configManager.getConfig().set("itradeshop.header", null);
+                hasUpgraded.add(true);
             }
 
             if (configManager.getConfig().contains("itradeshop.allow-explode")) {
                 configManager.getConfig().set(ITRADESHOP_EXPLODE.path, configManager.getConfig().get("itradeshop.allow-explode"));
                 configManager.getConfig().set("itradeshop.allow-explode", null);
+                hasUpgraded.add(true);
             }
 
             if (configManager.getConfig().contains("tradeshop.header")) {
                 configManager.getConfig().set(TRADESHOP_HEADER.path, configManager.getConfig().get("tradeshop.header"));
                 configManager.getConfig().set("tradeshop.header", null);
+                hasUpgraded.add(true);
             }
 
             if (configManager.getConfig().contains("tradeshop.allow-explode")) {
                 configManager.getConfig().set(TRADESHOP_EXPLODE.path, configManager.getConfig().get("tradeshop.allow-explode"));
                 configManager.getConfig().set("tradeshop.allow-explode", null);
+                hasUpgraded.add(true);
             }
 
             if (configManager.getConfig().contains("tradeshop.allow-hopper-export")) {
                 configManager.getConfig().set(TRADESHOP_HOPPER_EXPORT.path, configManager.getConfig().get("tradeshop.allow-hopper-export"));
                 configManager.getConfig().set("tradeshop.allow-hopper-export", null);
+                hasUpgraded.add(true);
             }
 
             if (configManager.getConfig().contains("bitradeshop.header")) {
                 configManager.getConfig().set(BITRADESHOP_HEADER.path, configManager.getConfig().get("bitradeshop.header"));
                 configManager.getConfig().set("bitradeshop.header", null);
+                hasUpgraded.add(true);
             }
 
             if (configManager.getConfig().contains("bitradeshop.allow-explode")) {
                 configManager.getConfig().set(BITRADESHOP_EXPLODE.path, configManager.getConfig().get("bitradeshop.allow-explode"));
                 configManager.getConfig().set("bitradeshop.allow-explode", null);
+                hasUpgraded.add(true);
             }
 
             if (configManager.getConfig().contains("bitradeshop.allow-hopper-export")) {
                 configManager.getConfig().set(BITRADESHOP_HOPPER_EXPORT.path, configManager.getConfig().get("bitradeshop.allow-hopper-export"));
                 configManager.getConfig().set("bitradeshop.allow-hopper-export", null);
+                hasUpgraded.add(true);
             }
 
 
@@ -235,12 +247,15 @@ static void upgrade() {
                 configManager.getConfig().set(GLOBAL_ILLEGAL_ITEMS_LIST.path, configManager.getConfig().get("global-options.illegal-items"));
                 GLOBAL_ILLEGAL_ITEMS_LIST.setValue(configManager.getConfig().getStringList("global-options.illegal-items").removeAll(Arrays.asList("Air", "Void_Air", "Cave_Air")));
                 configManager.getConfig().set("global-options.illegal-items", null);
+                hasUpgraded.add(true);
             }
 
             version = 1.2;
         }
 
         CONFIG_VERSION.setValue(version);
+
+        return hasUpgraded.contains(true);
     }
 
     public String getKey() {
@@ -255,6 +270,10 @@ public String getMappedString(String subKey) {
         return PLUGIN.getSettingManager().getConfig().getConfigurationSection(getPath()).getString(subKey.toLowerCase().replace("_", "-"));
     }
 
+    public boolean getMappedBoolean(String subKey) {
+        return PLUGIN.getSettingManager().getConfig().getConfigurationSection(getPath()).getBoolean(subKey.toLowerCase().replace("_", "-"));
+    }
+
     public String getPostComment() {
         return PLUGIN.getLanguage().getPostComment(Language.LangSection.SETTING, path);
     }
@@ -281,7 +300,7 @@ public String getFileString() {
         if (defaultValue instanceof Map) {
             keyOutput.append(section.getSectionLead()).append(getKey()).append(":\n");
             for (Map.Entry entry : ((Map<?, ?>) defaultValue).entrySet()) {
-                keyOutput.append(section.getSectionLead() + "  ").append(entry.getKey().toString()).append(": ").append(new Yaml().dump(entry.getValue()));
+                keyOutput.append(section.getSectionLead() + "    ").append(entry.getKey().toString()).append(": ").append(new Yaml().dump(entry.getValue()));
             }
         } else {
             keyOutput.append(section.getSectionLead()).append(getKey()).append(": ").append(new Yaml().dump(getSetting()));
@@ -301,6 +320,11 @@ public void setValue(Object obj) {
         PLUGIN.getSettingManager().getConfig().set(getPath(), obj);
     }
 
+    public void setMappedValue(String subKey, Object obj) {
+        String newNode = getPath() + "." + subKey;
+        PLUGIN.getSettingManager().getConfig().set(newNode, obj);
+    }
+
     public void clearSetting() {
         PLUGIN.getSettingManager().getConfig().set(getPath(), null);
     }
@@ -309,7 +333,7 @@ public Object getSetting() {
         return PLUGIN.getSettingManager().getConfig().get(getPath());
     }
 
-	public String getString() {
+    public String getString() {
         return PLUGIN.getSettingManager().getConfig().getString(getPath());
 	}
 
diff --git a/src/main/java/org/shanerx/tradeshop/shop/Shop.java b/src/main/java/org/shanerx/tradeshop/shop/Shop.java
index 3c7cf51a..6bdc4d44 100644
--- a/src/main/java/org/shanerx/tradeshop/shop/Shop.java
+++ b/src/main/java/org/shanerx/tradeshop/shop/Shop.java
@@ -725,7 +725,8 @@ public void setOwner(ShopUser owner) {
 	 * @return true if player has been set
 	 */
 	public boolean setUser(UUID newUser, ShopRole role) {
-		return removeUser(newUser) && addUser(newUser, role);
+		removeUser(newUser);
+		return addUser(newUser, role);
 	}
 
 	/**
diff --git a/src/main/java/org/shanerx/tradeshop/shop/listeners/ShopTradeListener.java b/src/main/java/org/shanerx/tradeshop/shop/listeners/ShopTradeListener.java
index 43d547f7..c4bba16c 100644
--- a/src/main/java/org/shanerx/tradeshop/shop/listeners/ShopTradeListener.java
+++ b/src/main/java/org/shanerx/tradeshop/shop/listeners/ShopTradeListener.java
@@ -134,6 +134,7 @@ public void onBlockInteract(PlayerInteractEvent e) {
                 return;
             case INCOMPLETE:
                 Message.SHOP_EMPTY.sendMessage(buyer);
+                return;
             case OUT_OF_STOCK:
                 if (shop.getShopType() == ShopType.ITRADE) {
                     break;
@@ -142,8 +143,6 @@ public void onBlockInteract(PlayerInteractEvent e) {
                 if (shop.hasSide(ShopItemSide.PRODUCT)) {
                     List<ItemStack> searchResult = getItems(shop.getChestAsSC().getInventory().getStorageContents(), shop.getSideList(ShopItemSide.PRODUCT, doBiTradeAlternate), multiplier);
                     Message.SHOP_INSUFFICIENT_ITEMS.sendItemMultiLineMessage(buyer, Collections.singletonMap(Variable.MISSING_ITEMS, searchResult));
-                } else {
-                    Message.SHOP_EMPTY.sendMessage(buyer);
                 }
                 return;
             case OPEN: