1. I agree that we like creature comforts. We lived in the Caribbean
on St Thomas for 2 years and learned quickly that there are certain things that make life easier in the tropics--most notably a generator
and AC! Though this adds complexity, it also (literally!) helps me sleep easier at night. I am not one who likens living on a boat to living in a tent.
AC can be occasionally a necessity but 99% of the time it's cool enough without if you're anchored out and not tied up at a dock in a marina.
2. Under-capitalized. Fair comment given what I have posted. We have several large assets and just because we could afford to buy--say--a 100k boat doesn't mean we want to. I tend to like things that appreciate (like real estate) and not depreciate--obviously a boat is the latter. While 20K is probably too low to find a good shell--I'd rather keep the looking lower. Would be lousy to fall in love with a boat thats outside of our (self-imposed) budget
Have been boating for 40 years and at one time was a yacht broker. In that time I've seen super deals come by about once every 5 years or so. A fixer upper that was sold for 10% of it's value because the owner was in jail, a couple of almost free boats sold by survivors when the owner died and several that were just projects that the owner couldn't complete. So super deals do happen but they are about as rare as winning the lottery (I think I'm starting to repeat myself here). So in your budget unless you do hit the winning ticket then a shell is what you will probably get. You admit your lack of skills so based on my observations the odds of the shell becoming a usable boat are down in the slim to none range. Of course you can pay a yard to do it but expect professionals to cost a LOT!!! Depending on the job and how labor intensive figure a minimum of 3X DIY to 10X DIY costs.
3. House rentals. This is a matter of personal risk and management IMHO. We rented our home in Phoenix for 2 years to great tenants but we made sure to do a background check, credit check, and collect deposits. We kept the rent reasonable because they took good care of our property. In Mexico
, we have a management company that takes good care of the condo and handles the rentals. We also are lucky enough to have close friends and family
to keep an eye on both places.
4. Lack mechanical experience. Yep, no question, and I'm not mechanically inclined. I am, however, interested in learning
See the comments above. To boat on a budget you need to be a mechanic, electrician, plumber and carpenter. If you have to pay people to fix, install, maintain or otherwise on your boat you will be way, way out of your budget.