I'm with the 'buy quality used' camp. There is such a buyer's market out there right now particularly for the boat you mentioned in your price range.

The depreciation in your first month with a new boat would probably pay for that moorage you aren't keen on.
I'd look at 1-3 year old boats and hire someone to survey/test the boat to get a high level of confidence going into it. You shouldn't have to look far to find some mint 50 hr. driveway queens out there.

Oh, and I would definitely go for mooring the boat rather than constantly trailering it. I think the easier the boat is to use, the more you are going to use it. If you're boat is at the lake ready to spin the key, its easy to jump in the car (rather than the truck and it's fuel?), whip out there and go for a quick spin. We took this approach and we are getting great, easy usage out of our recent boat and it's really paying for itself.
I do think you're fuel costs are low tho'. If you set yourself up to use the boat...which is why you would want it, then you're probably going to burning a bit more fuel. Another reason for a quality used.

My two bits.
BP