Yea, you'll need a new bellhousing. The bell housing on an AOD is non-removable

You can reuse your flex plate from the AOD. They make 2 different bell housings for a C4...you want a big bell housing if you're using the 164-tooth (AOD) flex plate. I believe PA's bell housing is designed to accomodate either flex plate size. PA uses uprgraded valve bodies in their transmissions, so no need for a shift kit. For your setup, I'd go with something that'll stall around 2600 - 2800 rpm for now. That might be big enough for you to get away with later on when you install a little bigger cam as well.
The 26102 is the pan fill whereas the 26101 is the case fill version. Basically, the only real difference is where the oil filler tube goes in. I'd go ahead and go with the case fill incase you decide to get real serious and go with a bigger
trans. pan down the road.
Absolutely only do this if you can afford to lose overdrive. With 4.10's, I'm turning 3500 rpm @ 65 mph.
Also, I'm already assuming you've got a good size
trans cooler on your car. If not, get one. I'll never run any automatic without one.