Say hi to your new best friend. Seriously, it will answer most of your questions'
What size jet you use is dependent on how you tune it. I'd suggest getting it to stock first. I will save you a ton of headaches if you don't have a lot of experience with these.
The stock carb comes with an 85 jet, but I don't see what carb you're using.
If you're using stock everything and use a pod filter it will probably get you running but you'll have to be checking temps to make sure you're not going to soft seize
If autochoke is working right now, just leave it.
Reminder that if it's an Iowa bike it's much slower and you'll have to do some searches through MA for any tiny increases in speed. You'll be going about 25 mph
There's tons of good info in here about Urbans.