diff --git a/CHANGELOG.md b/CHANGELOG.md
index e5b4f9e..0f8cbdf 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -3,8 +3,10 @@
 ## v2.29.0
 * **Change default configuration format to .ini**
   * Existing `config.json` files will continue to work and will not be deprecated
-* New, rewritten instructions for setting up and using the bot
-* Updated several package dependencies
+  * This makes the default configuration format for the bot much more approachable than JSON
+* New rewritten instructions for setting up and using the bot
+* New easy-to-use `start.bat` file for Windows
+* Update several package dependencies
 * Fixed incompatibility with certain Node.js 10 versions
 
 ## v2.28.0
diff --git a/src/config.js b/src/config.js
index 136a6bc..c9993c5 100644
--- a/src/config.js
+++ b/src/config.js
@@ -40,7 +40,7 @@ if (! foundConfigFile) {
 }
 
 // Load config file
-console.log(`Loading configuration from ${foundConfigFile}`);
+console.log(`Loading configuration from ${foundConfigFile}...`);
 try {
   if (foundConfigFile.endsWith('.js')) {
     userConfig = require(`../${foundConfigFile}`);
@@ -123,6 +123,7 @@ const defaultConfig = {
 };
 
 const required = ['token', 'mailGuildId', 'mainGuildId', 'logChannelId'];
+const numericOptions = ['requiredAccountAge', 'requiredTimeOnServer', 'smallAttachmentLimit', 'port'];
 
 const finalConfig = Object.assign({}, defaultConfig);
 
@@ -152,14 +153,6 @@ Object.assign(finalConfig['knex'], {
   }
 });
 
-// Make sure all of the required config options are present
-for (const opt of required) {
-  if (! finalConfig[opt]) {
-    console.error(`Missing required config.json value: ${opt}`);
-    process.exit(1);
-  }
-}
-
 if (finalConfig.smallAttachmentLimit > 1024 * 1024 * 8) {
   finalConfig.smallAttachmentLimit = 1024 * 1024 * 8;
   console.warn('[WARN] smallAttachmentLimit capped at 8MB');
@@ -212,6 +205,33 @@ if (finalConfig.newThreadCategoryId) {
   delete finalConfig.newThreadCategoryId;
 }
 
-console.log("Configuration ok");
+// Turn empty string options to null (i.e. "option=" without a value in config.ini)
+for (const [key, value] of Object.entries(finalConfig)) {
+  if (value === '') {
+    finalConfig[key] = null;
+  }
+}
+
+// Cast numeric options to numbers
+for (const numericOpt of numericOptions) {
+  if (finalConfig[numericOpt] != null) {
+    const number = parseFloat(finalConfig[numericOpt]);
+    if (Number.isNaN(number)) {
+      console.error(`Invalid numeric value for ${numericOpt}: ${finalConfig[numericOpt]}`);
+      process.exit(1);
+    }
+    finalConfig[numericOpt] = number;
+  }
+}
+
+// Make sure all of the required config options are present
+for (const opt of required) {
+  if (! finalConfig[opt]) {
+    console.error(`Missing required config.json value: ${opt}`);
+    process.exit(1);
+  }
+}
+
+console.log("Configuration ok!");
 
 module.exports = finalConfig;
diff --git a/src/main.js b/src/main.js
index 16d7058..5a29e70 100644
--- a/src/main.js
+++ b/src/main.js
@@ -35,18 +35,20 @@ module.exports = {
     console.log('Connecting to Discord...');
 
     bot.once('ready', async () => {
-      console.log('Connected, waiting for guilds to become available');
+      console.log('Connected! Waiting for guilds to become available...');
       await Promise.all([
         ...config.mainGuildId.map(id => waitForGuild(id)),
         waitForGuild(config.mailGuildId)
       ]);
 
-      console.log('Initializing');
+      console.log('Initializing...');
       initStatus();
       initBaseMessageHandlers();
       initPlugins();
 
+      console.log('');
       console.log('Done! Now listening to DMs.');
+      console.log('');
     });
 
     bot.connect();