Hello. Great question and great to see there is still some sense of adventure left in both of you.
I am 82 and the lady who shares her life with me is not far behind. We started "living aboard" in 1998. Since then we have 3 600 mile and another 2500 mile trip plus months and weeks in one marina or another and thousands of short trips.. I admit we are both pretty healthy for our age and have a fairly liberal cruising budget
. And we live a lot larger than we ever thought possible to do on that budget
. We are not limited to $500 a month.
First I would say that "living aboard" is very very individual. Some peaple almost never leave the marina. Some are in a different port every night. Some are almost never in port. Some have a winter spot and a summer spot. Almost an infinite variety of styles. Some of their slips look like they are transplanted farmers or gardeners. Some alternate between the boat and an an RV of some sort. Sone have no other transportation, many have a dinghy
and some have a car. Some have bikes and some some seem to have a whole bunch of things. So " living aboard" is a lot of different things.
And of course marinas
differ. Some virtually prohibit working on the boat, others are almost exclusive do-it-yourself boat building/rebuilding. Some are darned pricey and some are nearly free. Some marinas
have a courtesy vehicle that is nearly free. and loaner bikes.
And cruising grounds are as varied. I know people who trailer a small boat using it and a a tent or a camper and spend a lot of time in State and Federal forests for a few dollars a day and water
so clear you are temped to drink it straight out of the lake. I have even seen the like in the Keys. On the other hand I have been in slips next to million dollar vessels. In Monico I have been surrounded by dozens of 150ft yachts each burning more fuel
keeping the Air Conditioning
running for the night than I use in a year.
The point is there is an infinite variety or ways to go and do and enjoy it all. They are all - right. And fairly easy to change about.
In most cases, it you buy your boat with reasonable care you can always sell it fairly quickly for most of what it cost you. Sometimes even make a dollar or two. So it almost never needs to be much money
down the hole. So don't overly worry about making a fatal mistake.
If you learn to read the charts
and pay attention to the weather
and listen to the chatter about the dock
you will be able to avoid danger
and as well or better than the less mobile land lubbers.
Frankly, we have never had a scare. Now and then after it was all over we realized it could have gotten scary, but it did not. Perhaps because we were careful and prepared and reasonably skillful.
May I suggest that if you can, try to find a Catamaran
in you budget range. YOu will both like the stability of it. It isn't just the heeling us older folks mind. It is the rocking. You can't safely walk anywhere. I lean to a sailing Cat. When the weather
is right it is cheap
way to go. Even under power we tend to motor
along at 5 or 6 knots - all day on 10 gallons. Much better than 10 gal or more an hour. I have a frinnd who tows and lauches his 20ft gas powered boat cause it is so much cheaper to tow it at 10 or less MPG than run it on the water
. Course he is just weekending. On the other hand, there is lots of stink pot "bargains" out there.
And watch out for cramped beds. I want a dedicated bed
that is comfortable for the two of us.
Good luck . Cheers