Transom housing
 

Helping a buddy rebuild his transom assembly , the housing has some corrosion up by the swivel shaft seal, cleaned it up and now I am able to put the new seal in by hand anyone run into this? I hear it's kind of a common issue because the seal gets stuck on the pin, and as it turns it wears into the housing, any tricks on fixing it. Thanks.

Not sure how bad yours is but I was getting water in the boat and I found the pin seal was leaking. After I totally disassembled it and blasted it I quickly realized it was JUNK. 4K later I ended up buying a complete new HP assembly.
https://cimg7.ibsrv.net/gimg/www.off...3fbad5c2fa.jpg
https://cimg8.ibsrv.net/gimg/www.off...be38868e41.jpg
https://cimg9.ibsrv.net/gimg/www.off...8fd73a9e85.jpg

If it's loose on the outside... glue or marinetex it in

It's not junk, it's actually in mint condition. Other than that one spot right there, the seal goes in, but it's loose. I can put it in with my hand and pull it out.

Yeah thats a big money savings if you can fix that. My assembly looks like it came off the titanic.

JB Weld the seal in?

Ayuh,..... If you can get at it with a prick punch, I've tapped a few divots in bearing/ seal seats, which shrinks the diameter enough to hold a bearing race/ seal,.....