Id say you have 3 options.
1. Buy as big of a boat you can afford and leave it at a marina on the trailer. Show up, drop it in, use it all day and put her away. No need to tow.
2. Charters! They do all the work, you enjoy the day and you save a TON of money.
3. Make friends with people with boats and chip in some gas money and use a scrub brush well.
Trailering a light boat to use in the ocean is just risky. A "kicker" engine might not even push you out of the way of a freighter with a west wind and outgoing tide. Unless you're willing to work the bay and areas inside, a smaller craft only puts you in harms way. Maybe not the first or second time....but there will be that Oh Sh*t moment you may regret.
The again, what do I know? I bought a boat and took out a loan = not very bright!
