Agreed - the risk/reward seems off here. It will probably be fine, but you could potentially end up in legal hell and risk your family assets.

Why not a "parent" company you keep going indefinitely, spin off other entities as needed?

This all varies by jurisdiction of course, but last time I did something like this I filled out the paperwork myself and it cost a couple hundred only. Gets more complicated with more structure, etc. and any legal work you need - but you don't need to pay for that before it's justified.