You will definitely get a GREAT understanding of how the transmission works if you fix it yourself. Also, you'll not beat the crap out of the synchros b/c you'll know how big of a job it is to replace them. $150 sounds real cheap for a rebuild.
As far as a clutch and pressure plate go, you could go stock with a LUK clutch kit. It's very affordable as far as clutches go. That'll come with the Throw-Out Bearing, pressure plate, alighment tool and friction plate. (it might even come with a new Pilot Bearing).
I got the SPEC Stage II clutch in my car and it's a LOT heavier than stock, however, it'll grip like velcro.
Not fun in traffic, but like most things with performance, it's a trade off.
Don't feel too bad about tearing up the trans. When I got my first t-bird, I demolished the M5R2 in about 2 months. It was great!!!!!!!!! But, I definitely don't drive it like that anymore.
The synchros are there to slow down the one gear (the one you're leaving) and speed up the other gear (the one you're shifting into). So, there's a friction and "squeezing out of trans-fluid" action going on there. When someone first drives a 5-spd t-bird, it seems like it doesn't shift very well, b/c you'll be trying your darndest to get that shifter into third gear and it just won't go. I know I punched the dash a few times trying to slam it into third. Now, I try to not shift it at rpm's over 4000 and when I do, I give the shifter steady pressure holding it against the gear I want to go into. When it's ready, it engages. Forcing it into gear is just wearing the life out of the synchros.