Well I finally was able to take it on a test drive (finally got plates for it). Bought it on 12/31, 1/1 I already had the engine apart

No issues at all, new belt, pulleys, tensioner, and water pump all for $150.
In regards to my question I'm pretty sure I'm right on #1. The TB is pretty much a foolproof operation. If you keep the crank on TDC and the cams anywhere near the mark, as long as the marks on the belt line up with the marks on the crank and cam sprockets you'll be right. With the side-bolt tensioner you don't have much wiggle room, so if the belt is off by one tooth or the sprockets are off by a significant margin you won't be able to get the tensioner on. If you have a slight amount of slack between the two cam sprockets the tensioner and belt will take up that tension when you start turning the crank.
I won't call it an easy job but if you have the right tools, mainly a nice air impact to get the crank bolt off, it's more than doable. It ended up taking me 14 hours or so because I tried to halfass it and do the waterpump without removing the cam sprockets, which wasn't worth the hassle. I could probably do it in 4-6 hours if I had to do it again.