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.  

If you've chosen these two just because you like the Indy market, I'd recommend expanding your search to other markets and focusing on reputation and customer service/PM quality.

Be a good buyer so you can scale in your chosen market.

There's no specification whether or not the tenant would have chosen to renew if there wasn't a sale going on.  

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.

I am admititly not an expert, but I see there are some critical differences for me and for my chosen strategy as to why each market is appealing.

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.