This is not a time in their lives for you to decide to gamble their savings.

Then he told me the reason I was there was not just to drink and gamble with him but actually to meet his partner. 

There are still investors in TO, but there are lots of folks who are gambling as well.   

Account Closed I laughed uncontrollably when I read that comment!

If that were not the case, I would not have taken that gamble.2) Tenant moving from out-of-state and didn't have a job in NOLA yet, but did have longevity in his employment history. 

I would not compromise my screening standards but if you decide to take the gamble do not offer a term lease.

you should evaluate each deal individually, unless they are being sold as a package of some sort or it gives you some other advantage.you can use the 15k deal as leverage perhaps to lower the price on the second house. if you are not cashflowing at 150k-160k dont buy it, unless you wanna gamble on appreciation. also, by owning three homes next to each other you are increasing risk because all your eggs are in one basket.

If it covers much of the costs be thankful, if it produces a profit as well you gambled and hit the jack pot.

You're ALWAYS going to have the same problem whenever your mortgage payments are similar to what rent would be, because of all the EXTRA expenses that any property has.Just to remind you, if you rely on future appreciation, you're gambling.

If you get no cooperation, then you can gamble and close or walk.