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Phil - In my opinion, fixing up a trailer that is in that bad a condition is a waste of time and money. You will always still have an old, fixed up but valueless trailer. and you will still end up spending at least 1K on it before it's right.

Locate a Continental dealer in the Florida panhandle, and order a new all welded galvanized Tilt-frame keel roller CV-8-72 (2800# capacity), and you will be way ahead financially.
It may cost about $1600. I have this trailer under my classic Outrage 19.
See photos in the personal website link.