I think your core concept is sound. You might be biting off a little too much to do all that at once. It could be worthwhile to start a little narrow and then build out from there.
For me, I start businesses for a living (in the startup/venture capital areas). Plus, I have a fair bit of boating experience. If you need help with business plans, ideas for capital allocation, or just a general deep-dive discussion with someone who is good at debunking theories, I'd be happy to buy you a drink at Tavern 27 sometime (since it's right next to my weekend place) and offer you some free commentary.
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