as far as whats wrong with it from what the pictures show.....
1) looks like it's been hit in the front kinda hard?
2) I think the left front fender is from a 2+2, it looks like a bench seat in the pic? So not a 2+2.
3) Roof looks like a dollar store blue tarp
4) body looks pretty rough in the rear quarters.
5) Any attempt to even semi-restore to a decent driver status will put it close to $7000. That's doing a lot of work yourself and getting a buddy to give it a Mop'N Glow paint job. Unless your an expert at install on a convertible top it's a $2000 job itself. Needs body work, interior work to some degree, wheels and tires, etc.
If you seriously shop for one of these, they can be had for that money $7000 in decent driver shape(or maybe a bit more, but $8500 max) I mean solid driver, not a show car.
If it was close by me in Ontario I'd be scouting it out. But I know where there is a real decent 65 convertible road ready and looking good for maybe $5000.
I'm always watching these big convertibles. Not the easiest to find, but a few different ones a year show up. For my next one I'd like a 67-70 drop top. The older I get the more nostalgic I get about remembering as a young guy how much time I spent in them. Evening cruises on a hot night with the lid down suits me more now as I'm too old and bald for high noon sun!