Your trans will NOT bolt up, because the 2.8 has a different bolt pattern. The only V-8 that will physically bolt up to your trans is a Cadillac Northstar, though the '84 trans probably wouldn't last for long behind a V-8 anyway. Trannies in an S-10 that WILL bolt up to a small-block are from 2.5 4-bangers (the Iron Duke) and 4.3 V-6s. Good luck with your swap.
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Depends on what you are doing, But if its on the street or strip the answer is no.....
I had an 88 Camaro 5.0 305 cid 5 speed manual I put a 350sb with Carb. in it Or a Mustang any year there all good parts for both are readily available, tons of aftermarket parts easy to fix Very affordable I had it when I was 16 "first car" my dad drove it alot, I sold it when we moved There are also alot of good classic cars out there to choose from! Although there more costly - or buy a project car much cheaper & more fun