Ive had 4 NA's.
Looking at an NC or ND when the FD goes away.
Always loved the flickable nature, still more flickable than my FD which annoys me to no end.
Currently have a 1990 NA that has been..heavily modified suspension wise.
Worried about tires? 949racing.com make some seriously sick 6UL's, 17x9 in Miata fitment..check them out. Thats a lot of tire on an NA, especially at only like 17lbs per wheel...whish they fit an FD. Id have sets already.
The cons I see about the swap are what you've stated pretty much - remember that the getrag diff from a caddy is JUNK to begin with..so might as well stick to the 8.8
I have the original monster miata swap book laying around somewhere for the day I eventually swap one. I have a welded in cage and hardtop so that we can run on blackhawk and road america.
Unless its changed, you used to be able to run if you had a hardtop WITH factory hardtop mounts. There are the front latches, rear latches, and then if the car was ORIGINALLY equipped with a hardtop, there are 2 latches in the middle, 1 on the frame next to each seat - that was legal. if you didnt have those extra latches, it wasn't legal even with a hardtop.
Another possibility - depending on your electrical skill level... why not J Swap the NA? Honda V6..plenty of power, can use factory driveline/axles etc and with a tune..they can net damn near 300whp and 280ish tq depending on which J series you get. (think 2007 acura TL type S) and have a 6 speed that shifts beautifully. Hell, the cost is comparable to a flyin miata turbokit with the Hydra II ecu. Plus again, parts are still cheap and readily available. And honestly, Ive worked at Honda for 11 years...those V6's have pretty much 0 issues. Look at some of the swaps into older EG/EK civics, they are making crazy power on some.
Think about this as well - even if stuff brakes on the Miata...its cheap, easy, and FAST to get replacement parts. FC/FD not as much.
Sorry if Im rambling..Im at work had to do this piecemeal not all at once. I tried to hit main points.
For the J swap =
http://www.superfastmiatas.com/JV6%20Miata%20Kit.html