After playing a number of characters dealing with crappy equipment drops and rarely finding an upgrade, I finally decided to try making a set of trading characters to help the others through the game. Following the common advice as it were. First I got a Dwarf with ~35 Trading at level 2 and the difference is amazing, I can buy level 1 gear that makes a new character basically invincible until the 20's. +All Skills equipment is a major part of that.

I read on darkmatters that +2 All Skills appear in Silver, with higher difficulties having even higher values. I got another Dwarf to 20 so he can go to Silver in LAN games, with ~50 Trading. I'm still seeing a good amount of +1 All Skills, but have yet to see a +2. Is this pure bad luck or does this mod also have a minimum level to spawn on top of difficulty? And if so, anyone know what it is (bonus points for knowing the breakpoints for the higher ranks)?

This game is not balanced, it's difficult to have this game not broken.
A community balance mod is really needed, if you don't want to 'cheat':
edit your character, or create alt characters (like you did).

Actually a huge part of the fun for me in old games is figuring out strategies for how to make myself invincible or very close to invincible without actually resorting to using a cheat code. Even in modern mmo's the rush to "endgame" is partly due to wanting this nearly-invincible state. Don't knock it, it's fun. IMHO a game is broken if you can't find a way to import a character, or duplicate money or fix it so you have the full set of bonus gear at the right level for it... I mean, if it's totally random, you'll outlevel the set-bonus gear before you find it all. That's usually the hint that you need to think creatively.

This is a great hint the OP has given about trading. Thanks, I've read it elsewhere and I was like... um, trading, really? Another hint I have for it is... if you're starting out, get a class with AoE damage... the battlemage is easiest to play I think, get a combo with a double-aoe and you'll nearly never die. Just collect the mobs like lint, aoe, and then fireball the stragglers to death. Grin sadistically and repeat.