I am 67 and a USN VN and destroyer vet. I've seen too many people put their dreams aside and just survive for years. They achieve their dream only to have health
problems. You never know how much time you have.
DO IT! Do it now. Learn on the job. Other people have done it.
Technically I anchor all the time. When cruising I like to anchor for long times in secluded places and use a boat to run in for supplies. I stay at a Columbia
River private dock
in the winter that only has a gangway
at low water. So I usually boat to shore. I've never had a problem wherever I've anchored, for any amount of time. I use a Incinolet, so no discharge or holding tank
problems. But 1 kwh per flush. I burn my garbage except for recyclable items. I turn my waste oil
in at a fuel dock. The only garbage I haul is ashes.
Check out the garbage, sewage, and oil
discharge rules. It's much easier to follow the rules and keep the Coast Guard on your side. We're lucky to have them.
It's a harder life afloat, but beats any neighborhood I've ever seen.
Sometimes it's nice to have a moat around your castle.
On the Navy
side... I did steer. Too much! Because I usually was the best helmsman, I had to steer every time there was something interesting to look at. While the other QM's were checking out the scenery, I was in a steel
room, looking at a compass
. Now I use the autopilot
all the time. At sea, in bays or rivers. I don't take the wheel
until almost at the dock.