Todd, If you can find something to do and be your own boss, go for it.
Showing my age here, I have worked for myself for the last 35 years and haven't regretted a moment of it.
You seem pretty handy mechanically, did a nice job of painting your house so you must be good with your hands.
This is how I started out, anything that came along i had a go at, did a few courses on welding, carpentry etc.
You need a bit of capital to tide you over at the start before you make regular money, but once past that
inital hump you won't look back.
There's nothing like being able to say no to someone asking the impossible, or expecting you to jump through hoops.
It's a huge decision to make especially with a young family.
I started by doing it on weekends to build up a client base in the mechcanical maintenance field and eventually
turned it into full time employment.
Bit of a rant, but you can't beat working for yourself.
Cheers Gavin