1. Militia have always perplexed me... So I set three squads up and have them training in my barracks. I'm having them go weaponless to build wrestling because I remember reading somewhere that that's usually a good idea. Now, they've been training for at least 3 seasons(maybe a whole year), they're becoming quite unhappy, and their wrestling skill has barely moved. Is there something I'm doing wrong here? Should I just get them some armor and wooden weapons and scratch the whole wrestling step?
Unless they're Champions, dwarves hate training for more than a month or two at a time. There's also the issue that you probably have their training regimen set up such that all ten dwarves in the squad are required to be at training; if you look at the Schedule, the training orders will say Minimum 10 Dwarves or something like that.
This means the training session will only start once all ten dwarves are present - and getting ten dwarves in the right place at the right time is akin to herding cats. A good rule of thumb is 60% of the squad - unless there's only four or five in the squad. Highlight a training order and press Edit to change the number of dwarves required.
2. Another thing that has always messed me up as well. I do quite well at keeping all my dwarves occupied up until migrant wave 5 or 6. Once I get 50 or so dwarves, I don't know what the hell to do with them all. Is the typical application here just to ramp up all your processes, build your military, and have !fun! with a few of the peasants?
Megaproject.
Or, yeah, ramp up production, more squads of militia, make them all masons and build a giant stone tower... whatever takes your fancy. Or let them throw parties.
3. Is it worthwhile to have multiple stonecrafters going at once? I usually just set one on repeat and sell whatever he makes to the caravans. This alone will usually give me enough trade goods to buy whatever I want from the caravans. Am I missing anything, or is it just a "look at all my pretty trinkets!" kind of thing after that? Not that it would be a problem, my dorfs love their mudstone rings
Not really, unless you're low on wood. Stonecrafters can make stone pots, which function identically to barrels.