Downtime
Okay, I've had a look at the extant Downtime rules and the UA and even some people's homebrew and for now here's how I'd like to do it: Just chose what you'd like to do (story-wise) and don't be too concerned about the mechanics of it. I will try to rule fairly.
From what I've seen the main goals of Downtime is to gain allies, items, information, or money while managing risk and reward.
So here's your basic options (tell me if you think I've missed anything):
Earning Money
Honest Work
Running a Business
Pit Fighting
Gambling
Crime
Crafting Items
Gear
Weapons
Armour
Potions
Scrolls
Magic Items (Maybe Later)
Making Allies
Religious Service
Carousing
Guild Meetings (Civil Politics)
Attending Court
Other
Relaxing or Convalescing
Gathering & Sowing Rumours
Language or Tool Training
Buying & Selling Magic Items
I like the rules they're attempting in the UA with the 3 ability checks, so I'm going to ask for those no matter what activity you pick. Try to use different skills as often as possible, and if you use the same one, try to describe a different use for it.
For example, If you want to forge a breastplate you could roll Persuasion to convince a Smith to let you use his forge, Intelligence to pick the best quality material, and Strength (Smith's Tools) to bang the thing into shape. The result will allow me to adjudicate the cost of the job, or the length of time it takes you to finish it. (and if you run out of money or time, you leave it incomplete)
For another example, you could go carousing, and roll Charisma to be Persuasion to make some friends, Performance to get up on the table and sing a song, and Constitution to make it home without passing out. Again, I will inform you of your expense based on the rolls, and benefits you might gain, like new NPC allies.
Any questions? (Feel free to give me three checks that go with whatever you've already told me you want to do!)
BTW, I will actually get this started soon, I promise.