I'm sure this probably won't work, but thought I'd ask.
I have a buddy that just bought a new street glide and he had his bike punched out to 103" at the dealership. Now he has this complete 96" top end sitting in a box and is looking to sell it really cheap. He has the cams, heads, jugs, pistons, basically everything but I really don't think I can just bolt it all on to my 88" bottom end. or can I?

 

The 88" and 96" motors from HD are actually the same bore size, but the TC 96 has a longer stroke. So, no there is no benefit. Not sure it will even bolt up. Maybe someone else knows for sure.

 

cylinders and heads will work but no go on the cams and pistons. The heads alone are worth $250; I have seen them go cheaper but $250 seems to be the going rate. You don't gain anything with the cylinders; they are the same bore as your 88"; the 96" is achieved with the 4.375" stroke. However, you can avoid some down time by having the cylnders bored to fit new 3.875" flat top pistons. The heads are a real improvement, even out of the box but if you decided on some head work, you can also avoid downtime by having the headwork done before you tear the 88" top end down. Cylinders bored to 3.875 and heads done for new .030" head gasket and a set of bolt in cams and you are set. You will need to rejet if carbed or get fuel management system and tune if EFI.

 

There is no benefit to you buying your friend's parts that I can think of.
WARG is correct about the stroke.

 

Thanks for the response's guys.
Just to summarize, if I am wanting to bore my current cylinders and have some head work done, I can buy his stuff and have it done while mine is still on the bike, then swap out with little down time. Or I can just take my stuff and basically do the same thing this winter with longer down time, but it's winter, so who cares..

 

Yeah but, with the later heads, you really don't need to shell out the bucks for porting. You can hit 100TQ/100HP with the later heads. Just need minimum machine work to equalize chambers and deck for the compression sweet spot for the cam you choose. So, if you can buy the stuff for $300 or less, you are in good shape. It will cost more than that to port your stock heads. You can dump the cylinders/pistons and cams on Ebay for cheap and recover half of the $300 you spent. And you can do it all this winter.