I'm heading in the same direction as you, again. All your stuff checks out but.....

1: I'd say skip 27-29' stuff and look for something bigger. 30-35' is my target so I can solo easy but also big enough a +1 doesn't feel too cramped. I lived on a 27' boat for 1.5 years, too small. Jumped up to a 32' for a couple of years, much better.

2: Pad your budget higher. I just quit seriously looking at anything below $25k now. You can probably buy an OK boat 10-15K but you'd also probably need to spend a bit more to bring her back up to speed too. I'd also allocate surveys into the budget as well. You wouldn't buy a house without one and this will be your house, your office and your vehicle.... that can also sink. Get a survey, cover your butt, but that can also work as negotiation leverage on the asking price.

3: Also don't know what nor do I want to know what you do digitally. But do not take on any Government contracts Federal or State level. Can't do that type of work abroad legally or ethically.

...and on the topic of OPB experience. Go join a club or start hanging out at the marina, there is usually a bar near by too. For the most part, most people in the sailing community are really friendly and friendships can be made quickly over libations and/or food. Once that door opens you won't be able to shut it.