I definitely have to rebuild the hydromatic on my '56 model 88. It's been sitting since '77 and still leaks transmission fluid whenever i push it in or out of the garage.

Is it difficult to overhaul a these particular transmissions yourself? I know of a reputable shop in town but they said they might not be able to help me out. What do you guys recommend?

 

Depending on what is leaking. Not the easiest to work on, but not the worst. If it leaks from front, near bell housing, it could be a simple front seal. Not too hard to do yourself. Have to remove fluid coupling though.

I happen to have a 1960 Jetaway transmission if you are interested. Let me know.