We've already lost one we had under contract due to about $75K of termite damage (worst our agent has ever seen, apparently), so we're hoping for a softball here.

HUD is the worst of them to deal with.

Check with your title company ot your state to see if they'll charge transfer taxes.Many insurance companies charge higher premiums for properties in LLC, writing commercial policies instead of residential, so there's another costs.And using a Quit Claim Deed is worst way to transfer title. 

I figure the worst thing that can happen is that I don’t cash flow.

The worst item long term is that the seller had the roof replaced without replacing the skylights.

Cashing out 401Ks is probably the worst tax move possible.

Worst case scenario is that you give it a go 100% FT as a wholesaler and if you run out of money in 6 months, you can always get a job in IT again.Just not sure Id advise most people to quit a job for real estate if their real estate wasn't generating any income at all yet.It sounded like you were putting in some pretty good hours with the real estate investing.

Worst case scenario he doesn't sign and you are in the same place you were when you started the conversation.

In a worst case scenario your family comes first, and having your home free and clear will maximize your family's safety.As far as using someone else's money goes, the bank's money would be a good candidate for that risky position.

Run the numbers at the worst point in the cycle for the worst duration in the market you are looking at while paying attention to the reality of the future (i.e. if the local market is heavily dependent on lead mining and lead mining just became illegal, probably not a good risk, everything being equal).