Some ignorant newbie questions

I've just got myself a 1990 Mustang GT. I'm new to Ford in general, and fairly new to EFI (I had a 2002 Camaro, but I barely tinkered with it, I'm much more used to Carbureted and few electronics), so I have a few ignorant questions.

1) The car is an AOD, and it's staying Automatic due to physical limitations and Connecticut State regulations. Has anyone heard of, conceived of the idea or know what kind of a nightmare it might be to try and cram the new 5R55S transmission out of the '05-'06Mustangs into a Fox? I know it would at least take a lot of electrical crap just to get the car to shift right seeing as how it's a fully electronic transmission and I don't even know if it would bolt up (probably wont) or if a custom bell housing can even be made to get the job done. I just like the fact that it's much more aggressively geared then most Automatics.

2) Over the winter, I'll be working on an engine for the car. My first REAL engine project (so expect a lot more ignorant questions to come, heh). I want to start with a brand new DART Iron Eagle block and working from the ground up. In general, I plan to spare no expense on the internal. The question is, I plan to throw an Aftercooled Vortech V-2 SQ supercharger on top. What is a realistic notion of how much compression vs how much boost you can run. Example: Could you run 17 lbs on 9:1 compression or 10 lbs on 11:1 compression, etc. I'm just looking for a rough estimate as to how much compression to build the engine to versus how much boost I want to run. Also, what's a realistic notion of how much boost you can run without doing anything too outrageous to the car thus making it undriveable. In other words, I want to be able to run mostly high grade pump gas and such.

Thanks in advance,
Geoff

I know the AOD is alright. I just like the really low gears on the 5R55S and the fact that it's a 5 Speed Auto geared more like a manual. I imagine it gives the car a snappier feel, so I'm curious if it could be fit into a Fox.

As for boost, I definately want to keep it to a level where I can run relatively normal gas.

I went to a local speed shop and talked to them about a few aspects of the project so I could get some input from people who know a good deal. One of the things we ended up discussing was the transmission. The bottom line is that it would be POSSIBLE to rig the 302 up to that transmission... however it would be such a nightmare as to not even begin to be worth it. Essentially I'd have to do something silly like rip the whole computer out of a brand new Mustang, install it with the Trans and then reprogram the entire thing to trick it into running the 5.0 properly. Not something I feel like getting involved in, so I'll be sticking with AOD.

Thanks for the help,
Geoff