You'll be fine. You've got a lot more going for you than most have in the past thanks to sites like this and the www in general.
Getting rid of stuff is difficult to say the least. In the end I saved art, and some tools stored at my brother's place.. and gave most of the things I had to charities. I was 43 unmarried and no
children... which is quite a different thing.
Once out there I realized how little I needed... clothes and possession wise. I acquired small art for the
boat... but mostly my stuff was "spares" hahahaha. Getting on and off a
dock,
anchoring and so forth was something I needed to feel completely comfortable with.. unassisted.
When there are no
boats or hazards around you can fiddle about... assuming the conditions are conducive. But making mechanical
repairs in a seaway
single handed is not easy.
Make your passages with favorable forecasts. They don't always
work out... but forecasting is not bad.
Most important for peace of mind is good secure
anchoring. Good
anchor, strong chain, good
windlass and good technique.
I like your
mast electrical plug idea...
Good luck! You'll be fine... better than fine!