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
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
Good luck! You'll be fine... better than fine!