Lost compression on cylinder 5

[60 toy ota]

On the power steering note, I do have a leak in that area. I think it may be from the reservoir, that’s a common problem right?

It is, but I'd say the high pressure line is even more so.
You'll want to replace the tranny lines too if they're original. Once they've been softened by time and oil leaks the stress of R&R can break the fibers inside without looking worse for the wear externally, that is until they rupture under load.

 

[clx16]

The reservoir leaks on mine a little. I have a new one to put in but haven't yet. All other hoses were changed. So yeah I think it is a thing.