Incomplete, but I want to make sure the ideas I have here don't get wiped. Sadly this commit won't compile.

src/scanner.c

@@ -37,7 +37,8 @@ List* GenerateTokenList(const char* source) {
                 AdvanceScanner();
                 break; //Ignore whitespace
             case '\n':
-                token = CreateToken("^", NULL, Line, LineEnd);
+                token = CreateToken(Line, PunctuationClass);
+                token->Value.Punctuation = NewLine;
                 AddListItem(token, sizeof(Token), tokens);
                 AdvanceScanner();
                 Line++;
@@ -95,24 +96,20 @@ Token* ParseNumber(void) {
     if (length == 0) return NULL;
 
     char* lexeme = calloc(sizeof(char), length + 1);
-    long* value = calloc(1, sizeof(long));
 
     if (!lexeme) {
         fprintf(stderr, "Failed to calloc space for number. %s.\n", strerror(errno));
         return NULL;
     }
 
-    if (!value) {
-        free(lexeme);
-        fprintf(stderr, "Failed to calloc space for the raw numeric value of a token. %s.\n", strerror(errno));
-        return NULL;
-    }
-
     memcpy(lexeme, &SourceCode[start], length);
-    // Setting the base to zero means the function will pick the base.
-    *value = strtol(lexeme, NULL, 0);
+    
+    Token* token = CreateToken(Line, NumberClass);
 
-    return CreateToken(lexeme, value, Line, NUMBER);
+    token->Value.Number = strtol(lexeme, NULL, 0);
+    token->Lemexe = lexeme;
+
+    return token;
 }
 
 Token* ParseDirective(void) {
@@ -133,12 +130,17 @@ Token* ParseDirective(void) {
 
     memcpy(directive, &SourceCode[start], length);
 
+    Token* token = CreateToken(Line, DirectiveClass);
+
     if (strcmp(directive, ".db") == 0) {
-        return CreateToken(directive, directive, Line, DB);
+        token->Value.Directive = DB;
+
+        return token;
     }
     else if (strcmp(directive, ".org") == 0) {
         fprintf(stderr, "[Warning] Org is not a supported directive.\n");
         free(directive);
+        free(token);
         IgnoreLine();
         return NULL;
     }
@@ -178,7 +180,9 @@ Token* ParseString(void) {
 
     AdvanceScanner(); //Consume the trailing double quote.
 
-    Token* token = CreateToken(lexeme, lexeme, Line, STRING);
+    Token* token = CreateToken(Line, CharacterClass);
+    
+    token->Lemexe = lexeme;
 
     return token;
 }
@@ -194,7 +198,8 @@ Token* ParseIdentifier(void) {
 
     if (length == 0) return NULL;
     
-    TokenType type;
+    Mnemonic mnemonics;
+    Registers reg;
     char* lexeme = calloc(sizeof(char), length + 1);
 
     if (!lexeme) {
@@ -204,14 +209,33 @@ Token* ParseIdentifier(void) {
 
     memcpy(lexeme, &SourceCode[start], length);
 
-    if (IsOpcode(lexeme, &type)) return CreateToken(lexeme, lexeme, Line, type);
-    if (IsRegister(lexeme, &type)) return CreateToken(lexeme, lexeme, Line, type);
+    if (IsOpcode(lexeme, &mnemonics)) {
+        Token* token = CreateToken(Line, MnemonicClass);
+
+        token->Value.Mnemonic = mnemonics;
+
+        return token;
+    }
+    if (IsRegister(lexeme, &reg)) {
+        Token* token = CreateToken(Line, RegisterClass);
+        token->Value.Register = reg;
+
+        return token;
+    }
     if (lexeme[length - 1] == ':') {
         lexeme[length - 1] = '\0'; //Bit hacky, but this makes the parser's job a bit easier.
-        return CreateToken(lexeme, lexeme, Line, LABEL);
+        Token* token = CreateToken(Line, LabelClass);
+        
+        token->Lemexe = lexeme;
+
+        return token;
     }
 
-    return CreateToken(lexeme, lexeme, Line, IDENTIFIER);
+    Token* token = CreateToken(Line, IdentifierClass);
+    
+    token->Lemexe = lexeme;
+
+    return token;
 }
 
 char PeekScanner(void) {
@@ -250,18 +274,30 @@ int IsPunctuation(char c) {
 }
 
 Token* ParsePunctuation(char c) {
+    TokenPunctuation punctuation;
+
     switch(c) {
         case '[':
-            return CreateToken("[", NULL, Line, LBRACKET);
+            punctuation = LBracket;
+            break;
         case ']':
-            return CreateToken("]", NULL, Line, RBracket);
+            punctuation = RBracket;
+            break;
         case '(':
-            return CreateToken("(", NULL, Line, LPARAM);
+            punctuation = LParan;
+            break;
         case ')':
-            return CreateToken(")", NULL, Line, RPARAM);
+            punctuation = RParan;
+            break;
         case ',':
-            return CreateToken(",", NULL, Line, COMMA);
+            punctuation = Comma;
+            break;
         default:
             return NULL;
     }
+
+    Token* token = CreateToken(Line, PunctuationClass);
+    token->Value.Punctuation = punctuation;
+
+    return token;
 }