The parameters are set heavily in their favor to minimize their risk of having to pay out.So you can pay for their services and gamble that you will be that 1 in 1000 customer and come out ahead, or you can do everything on your end to limit your chances of needing their services, and keep the $$ in your own pocket

Just seems like such a gamble.   

That will be a big part of choosing the next steps.Some lenders will do a short-sale without missed payments, but usually with a hardship (illness, job / income loss, etc.).If there's some balance between appreciation and the current short fall in the LTV, you might consider subject-to or just make up the short fall at closing and avoid the short sale gambling on appreciation to make you whole (not recommended).Dunno ... too many unknowns ...

Should you buy with a negative cash flow in markets like California or Las Vegas and gamble on appreciation (in the early stages of a declining market)?

some of them don't require any due diligence, but it is nice to have a flexible client.however, i just joined this site today and don't want to seem like i am spamming, but i am sure you will find an investor.

Way too big a gamble for all but the richest people.

If it is, and you have no reason to fear for its long-term safety (which I understand is a big question in Illinois,) I wouldn't cash out - a guaranteed monthly check sometime in the future is better than a gamble, even on real estate.

Sure, if you don't mind gambling with your future.

Otherwise it’s just gambling!

Buying thinking that the next recession won’t affect real estate is just gambling in my opinion.