What do you think is the fastest set up for my TBI 305 5-speed (not counting a engine swop) ? Everything is stock right now. I am trying to make a list and would like to get the most for my money. I have about a $1000 to spend and will be doing all the work myself.

Start with bolt on : Headers and 3" all the way back. Gut your cat, and open up your air filter. Putting a function scoop/cowl on wouldnt be a bad idea since the stock hoods are a hot box and your engine is breathing hot air with the open element and no scoop/cowl. Theres your grand... You need a good $5000 to make a LO3 a true respectable motor. Mine will include Vortecheads, performer Manifold, open element sealed to a cowl to breath fresh air, LT1 cam, headers to 3" Y. No cat and 3" all the way out. Plus all the tuning. Transgo shift kit and corvette or billet servo is a good idea too.

PS: Forgot you said 5speed

I've rebuilt 350's for less than a grand, headers and catback shouldn't run you more than 500-750 unless your buying ceramic everything. I would do the exhaust and a set of gears. This should get you deep into the 15's if not 14's. You might want to look into DIY tuning before you get much deeper into modifying your LO3.