is it possible and if it is hard to swap an 88 3rd gen 305 and trans to a 95 fourth gen roller cause my 3rd gen body has seen newer days

You actually want to put the 3rd gen TPI into a 4th gen? That's a first. Lots of 4th gen engines into 3rd gens....

So...Is it possible? Well, other than adapting the 3rd gen ECM to the 4th gen body, pretty easy swap.

The mount locations/bolt pattern of the Gen I small block and the LT1 is the same, and so is the bellhousing bolt pattern and flywheel, so it will drop in as far as that goes. Same goes for exhaust. The biggest problem will be the accessories - the PS pump is on the passenger side on the LT1 cars/motors, and on the drivers side on the Gen 1 motors. Custom lines will have to be made for that. Same with the A/C if you use that.

4thgen hoods also have VERY limitted hood clearance, so anything taller than a TPI will likely not fit.

make sure your dizzy's good, as you probably wont see it after engine's installed.

http://www.bratmotorsports.com/96turboformula.htm

you can see the mods done to the cowl for clearance

well actually its not tpi in my car if that makes any difference

Well, whatever setup you use, you should keep it as short as possible, or get some kind of taller hood for the 4thgen. They have VERY little hood clearance - I'd be surprised if a stock 3rdgen Qjet and air cleaner would clear a stock hood. I put a Harwood 3" cowl on my '97 and it would have lots of room now, but it woulda been really tight with the original flat hood.