And to your fear of the unknown hell you bought your first boat....HUGE unknown yet you did it. Put on your big boy panties and dive in. This the season; you ain't gonna get better weather than the next couple three months for this kind of project and you can be on the water for late summer...
The boat already looks like crap, get over that. Do the repair and paint over the crappy areas. Don't have to match. Make it neon yellow. Midnight blue. Barbie pink, whatever. Just tape off an area and paint.