Along with the usual bush and grass jobs people would have us do house cleanouts, cleanups, and basic maintenance, so I know that I would not be totally jumping into unknown waters.

The Guarantor agrees to be personally liable under the terms and obligations of the Debtor in this Agreement.Borrower's Known Assets: Home in Florida with 300K+ in equity, bitcoin in wallet $500K, 401K $500K+, two small businesses (equity unknown).I hope this is enough info to get the conversation started.

Don't use some unknown entity from another state that no one here knows.I think both of these companies will shoot you straight. 

How do you underwrite an unknown cost?  

How it breaks across trades is unknown. 

But the today the high interests and the unknowns in the market makes it very risky.

And do it with a smile and energy unknown to most. 

@Henry Clark The fear of the unknown is stopping one of my co-workers from becoming a homeowner.

That’s not to mention the factors that are unexpected or completely unknown that can ruin a deal.6.

These answers may seem obvious to you all, but remember-- I've never done this before, so it feels like a huge unknown risk.