It can be done in your budget on a sailboat, don't know about a
trawler.
Fuel costs are much higher. Used sailboats are much less expensive -even free sometimes.
Our budget is similar to yours, and we do it. But we stay on
anchor most of the time and don't stay at
marinas if we can at all help it. We skimp and rarely eat out,
cooking from scratch without meat. We live VERY frugally. Lots of rice and beans and grains bought in bulk. Nothing fancy or expensive. It isn't a luxurious dream
retirement lifestyle on the beach.
Maintenance costs are higher for a boat that moves compared to one that stays in one place all of the time But if you are very handy and know how to fix and adjust stuff before it breaks hard and gets ruined the costs are not all that bad. It is mostly labor and minor supplies. But you have got to WORK at it and not let it get ahead of you. The
learning curve is steep.
Mistakes or being lazy costs $$$$$
We don't have pressure water or hot water, no
refrigeration and a lot of other expensive to maintain systems we go without.
We are full time cruisers who migrate up and down the
East Coast, we don't stay in one place all year, and don't have heat or AC. So we really need to move and adjust the latitude to match the temperature that is comfortable outside without heat or AC. This summer we got as far north as Montreal to beat the heat, so yeah, we put some miles on. We don't
head far south until the
hurricane season is over. Right now we are still in
North Carolina.
Fuel costs are not much since we are a sailboat and always try to have a sail up, even on the
ICW, which means we burn much less than one gallon per hour when motorsailing yet still maintain 7 knots on average. Usually 1/2-gallon ler hour on average. I imagine even a small trawler would burn at least twice that, if not much more. A gas engine(s) will burn way more than a
diesel too -which I doubt will be in your boat budget.
Insurance is expensive -especially
medical insurance. We aren't old enough to get Medicare yet. It's all part of our budget and even Obamacare is damned expensive. You could always go without but what happens if you get cancer or other curable but really expensive disease? Just die because you can't afford the cure? Go intonthe poor house? Skip out on bill-collectors following you for the rest of your days?
Boat insurance is expensive too, but you need it many places. Some marinas won't even let you in without at least liability, and there are times you will need to stop at a marina for
repairs or haulout that can't be done at anchor.