Moss,
I'm a chief. Great food for thought though. Much like your sister, I enjoy the creative / problem solving part, but will tire if it becomes repetetive. One thing that attracts me to the remodel / building business is that every job is different (except for tract housing).
I don't mind being the indian as long as I'm the chief who gave the directions...
I'm fortunate that I'm in a good place financially that I can afford a substantially reduced salary for a year to get the business off the ground.
Initial plan is to carry the medical insurance through my wife's employer, but I'm pricing high deductable insurance as part of the business plan (as well as liability, disability etc.) I already have term life (I'm worth much more dead than alive

).
You can minimize your financial risk by incorportating or LLC (Limited Liability Company) - Personally you are only at risk for the money you put up to capitalize the company - truck, tools. working cash etc. A sole proprietor is personally liable.
The idea of "contracting" for my current employer is interesting. The problem is that in my current role they would have hired me to improve their business, but aren't willing to make any changes...

It's as if you were paying me to build you a new deck, but wouldn't let me start.
reg
JLC & finehomebuilding have online forums - though they aren't as good as tbn is at tractors.
Everyone
I'm meeting one of my networking contacts tonight for dinner - I'll report back.