In October I bought an 86 Trans Am for about $3000. Since then I've replaced the water pump, all the belts, the lower hose, the radiator, the front seal in the transmission, and I just took it to the shop to replace the torque converter (and hopefully NOT to also rebuild the transmission - it crapped out the other day). It also needs wheel bearings. It's starting to feel like a money pit. I'm not planning on doing any modifications to it, just maintaining a powerful everyday driver, and I'm beginning to wonder if I should take my friend's offer of $5000 and go buy a newer one. Any thoughts?

 

Five grand is pretty good - you could always buy another third-gen and use the leftovers to fix it up real good. Or what you said, buy something newer. How much newer? Just make sure he's for-real when you negotiate the price, although there's not much negotiating at 5000 needed!