The skill trainer isn't broken. Upgrading the skill trainer just increases the number of times you can train from him. So at level 6, you can train 6 skills per character from him. It's still 1 skill learned per usage.
The dragons are easily killable with the right setup. I've done it on Day 46. I imagine if I had gotten better guns earlier in the game, I could have done it before that. My basic setup was a noble with a rapid bowgun with speed mod + bowmaster and 3 grenades. 2 sheriff allies with maxed doc holiday and auto shotguns and a sniper. Killed off all the dragons before they got off the first shot.
Esperlin: Blacksmiths do sell mods and weapons, look into upgrading the shop. Gold is easy to earn if you invest in the economy (chickens/museum, etc.) Bosses have the right amount of hp, look for guns that are good vs. armor and don't waste your time shooting at them when they're using a shield, they're fine. There is an upgrade for extra AP: active and some achievements. Henchmen are fine, they're a crutch when you need it for a few days, it's not meant nor needed to carry you the entire game. Sisters are crazy powerful, they don't need to respawn, just buy more if you want it to last the whole day.