Investing for appreciation is like gambling.

Tonight, he just called very meekly to apologize for disturbing me earlier on when his phone spammed me with calls.

The HOA decides to raise dues, the rental cap is met, a special assessment gets slapped on your association and BAMN your cash flow just went out the window.Condos are, in my mind, a gamble, your investment is at the mercy of others decisions and often those other peoples interests aren't in line with mine. 

I once borrowed from him where he made me sign a statement (one of 100 statements) that said if I gambled away the loan funds in Vegas that I was still obligated to pay him back.

I did some research for a client of mine regarding a raffle of cosmetic surgery and raffles appear to be gambling (at least in the state he wanted to do it).It may be different if you were doing it for charity -- as in, all proceeds go to the charity and no one profits from it.

I'm interested in investing, not gambling, so I'll stick to reading until I'm ready.

I would feel trapped in  my home (cash poor) and feel like I was gambling on appreciation but I am a chicken by nature .

It is always a gamble you take on any offer you accept.BUT -- to reduce your chances of the buyer not qualifying for a loan, ask to have the buyer cross-qualified by a lender you know, like and trust.

It's a gamble as some can be damaged but it's usually a good deal.2.

However, if it will stretch and stress you to the MAX, it is not worth gambling on future appreciation as I am sure you would make a nice profit selling now.....that's my two cents.