Many people are gambling on the market.Fund managers are having a party with cheap money floating around everywhere as well.I'm very conservative and young, so if I have to wait until the end of the year or into 2014 for a correction to buy back in that's OK with me.

If I make 9% in the market I'm doing a great job, but if I make -9% I'm screwed, so that seems like a huge gamble compared to a guaranteed ROI. 

Things like that should be pretty minimal in the grand scheme.That's assuming the HOA in question has good financials and an adequate reserve fund, so if they do suddenly find out they need a new roof, they don't have to hit the owners with a big assessment, but that's a whole topic by itself.The real gamble is how long this guy is going to be around.  

But it's okay, because if his gambling winnings aren't sufficient to pay the rent his family will give him money. 

But it feels a lot like gambling to me, and I'm a terrible gambler. :)I hope you'll take this in the spirit intended, but it sounds like you are trying to keep all your options open.

Mainly because I am not good at it, and feel it is just gambling.

She won't be able to keep up with his spending, or gambling problem or whatever it is.  

I think maintaining open lines of communication with the tenant and family will help the situation tremendously.You're taking a gamble, but it's one I would probably take too.

Second, if they've been there forever,  do u want to gamble a possible long term tenant but with low rent or higher rent with possibly a lot of turnovers? 

It is a quadraplex and so if I got a full occupancy then all the effort will have ben worth the gamble.