It really depends on your comfort level working with fiberglass and what you hope to get out of the boat.
If you just want the job done, then $500 for a shop to do some minor repairs and clean up doesn't sound like it's way off base. I would certainly find out some specifics on what they're going to do (repair processes, new gelcoat, etc.?).
If you're handy, then I would think you can do most of what you described yourself. Cleaning, polishing, and waxing the boat will make a huge difference, it just takes some time and effort. Small delam repair and small fiberglass patches aren't too difficult, but they take some time and materials, and if you want a cosmetically perfect repair, then I would leave that to a pro. Bottom jobs are also, pretty straight forward, but they take time and there is material cost. Gelcoat can be rolled or brushed on the bottom, and if you're not too worried about looks, you can just give it a quick sanding after it cures and you're good to go.
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