Dude,
we're sorta similar boats.
I am not putting anymore money into my car (94 EX auto) except for maintenance, although I do have i/h/e. I thought about tearing down the motor and going NA with custom pistons, rods etc and a tranny swap, but in the end I'd spend close to 10 grand and still be dreaming about getting a truly fast car. So I decided that for the next coupla years, I'm gonna run my car into the ground and either swap to a prelude's 5 spd with a LWT flywheel when the auto blows; or get a stronger platform to build from ... depending on where I am in life in terms of buying a house vs needing a new ride.
Don't spend the money on just i/h/e. It will simply give you the bug to mod and you'll still need to get a tranny at some point....
Option three will get you to 300 hp faster and more reliably too bad $$$$$$$$$
I think a tranny, ltw fly and headers (no other mods) will be decent cuz it will keep you excited about the car, but not put you too far in the hole.
Option 4 is the smart money, but there was a reason eunuchs guarded the harem: its really hard not to blow your load when you have the chance for a ton of candy.
noel