New cruiser ready to pull the trigger

[Imbroglio]

Ive had enough of the hard.
Next year I will sell my Portland OR house and buy a boat to disappear on.
Plan to base out of Panama (minimal hurricane issues) for a couple years while I relearn to sail (sailed lots in the early nineties, then started racing motorcycles. Only one pricey hobby at a time) and explore the Caribbean and south america. Then head somewhere else.

The goal is liveaboard, a little chartering for extra cash and company and see the world.
Budget is small but I have skills to rebuild a boat.
Looking for 37-42ft ish.
What would you recommend I search for?
What ya got?

[Tillsbury]

Chartering is the word that sticks out there like a sore thumb. You will need to choose and equip the boat specifically for this, and ensure that you can insure it appropriately. That won't be easy, especially on an older boat. Getting the paperwork and licences required especially overseas will be the next level of complexity. Unless you know exactly what you're doing you may have to delete that part of the plan. If you plan on doing it under the radar then choose a boat that's cheap enough that you don't mind it being confiscated.