Re: US Navy Veteran_New to Sailboats_Need your Honest Knowledge and Experience_Thanks
Plan on some solar panels that can be tilted to follow the sun.
Most people with your sort of dream find that they will anchor for periods of time in out of the way spots. Having a planing dink enables you to get to civilisation when you need to although a sailing dink works as well, it just takes longer. The raft idea is bad, you will get caught out and blown out to sea.
Where do you plan to be for hurricane season?
There are boats around in your price range. Something around 37 - 40 ft. A CSY 37 type A would be high on my list. Built like a brick outhouse.