how easy, or hard, would it be to swap my 305 tbi out of my 88 trans am to a LS2.what would i need to get for it.would a LS1 be easier?what would be cheaper

 

Hi Grizzlybear. It doesn't look like you've been here long so welcome to TGO. If you look at the top of the engine swap forum there is an LTX LSX category where most of the info you need is. There is also a FAQ thread there. There is also an LS1 sticky thread with some good links right below that.
To give you a short general answer, the easiest way to perform the swap would be to find a donor car so you can yank the engine, tranny, ECM, harness, fuel pump, accesories, etc. There are aftermarket companies that make some of what you'll need if you want to go that route. If you want to have AC you will have to modify your front cross member and you will have to fab some of your exhaust.
ls2 engines GENERALLY cost more
Look through the FAQ in the LTX LSX heading and then if you have something specific that is not covered post your question there and I'm sure some of the guys that have done the swap will jump in and help you.
Good lUCK.