Initial inspection of A500
If it were me I would rebuild it do to age and pulling around a 5400 lb truck for who knows how long. Their so easy and cheap to rebuild it's not worth the extra work to yank it back out later to do it and I can almost guarantee you will have too running it behind a stroker unless you never get on it. The good thing is it looks to be in good shape so rebuilding it shouldn't be all that expensive but I will echo the comments on using Red Eagle clutches and a good band. Like already mentioned it's basically a 904 on the front end. While their stout the torque of a stroker will trash them if their not hopped up some. Get the clearances tightened up too. I know I'm echoing a lot of comments already made but just wanted to throw in my experience of 38 yrs. of rebuilding torqueflites. I have a 408 in my car making about 475 hp and it weighs 3440 without me and I did up a 904 for it 5 yrs. ago just the way I said and am running a 4000 stall and drag radials and have literally beat the crap out of it and it still works as good as the day I put it in. Cooling is key to a long lasting trans too. Make sure to keep it cool. Mine never goes over 180 on a hot day when I'm dogging it