A guarantee to lower the price is simply an invitation to raise the price as high as a seller can, with or without adding any value, and gamble on an appraiser bringing in as high a value as possible.  

This seems like a reasonable gamble.

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 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.

True that offshoring has happened in several tech areas over the years but it’s limited to people below a certain level of skill set and has not worked well beyond a certain point because of cultural and time zone issues.