completely reworking the hulls

So i have a '80 Hobie 16 that needs a lot of work on the hulls. They are filled with chips and dings and a bunch of spongy spots. My plan is to first, drill holes in the top of the hulls around the spongy spots to inject resin to reinforce the first layer. Then on the particularly bad spots, I was going to put a fiberglass sheet over top for extra reinforcement. Then, I was going to cover the hulls in resin because they often make unsettling cracks and creeks. then sand it down and paint it. but I have some questions.

-do i need to re apply a gel coat after the paint?
-what do I do to repair the chips in the hull?
-how do i get the high gloss shine after painting?
-my hobie sits on a lift on the side of a dock and is in the hot southern virginia sun almost constantly, I need a lot of UV protection, any thoughts on that?

You either use gel coat or paint. So, answer is no.
DEpending on size of chips, you may fill small nicks with any off-shelf filler (West Marine, Jamestown), or short-haired filler (marine bondo) if bigger chips.
Wet sand (look up grits but I think you need to use 1000, 1500, 2000 to get the high gloss finish then buff then polish.
Keep it waxed, or covered, but I've had less problem with fading paint (good paint) than factory gel. Maybe thats not normal. Two part Urethane, Awlgrip, something of that quality.
Plan for lots of sanding

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H18, H17 & Various motor boats

sounds great thanks! Any recommendations on paint? what brand have you used that works well? also how much thinner and what type do I use so I don't get paint brush strokes?

Interlux Brightsides paint works well. It's easy to apply with the roll and tip method. Go to YachtPaints.com for more info.
Most of the work is in the prep. Don't try to short cut. Do it right and the boat will look like new. Do it wrong and the boat will look like crud.