I wouldn't worry as much about the age as I would what it would cost, how much it would rent for, how well it is built and when major repairs will be needed (ie how long will the roof last).Also for the two-are they both condos (ie strata/condo fees) or is one freehold and the other a condo (ie one has condo fees and the other doesn't)? 

The vast majority are using their equity to increase their portfolio with small multi family.  

Self-employed types always represent a major problem when it comes to verifying their income.

Hello -- I need to do a major rehab on a rental property that will cost about $50k-60k but the contractor does not want 1099 and wants nothing to be reported to the IRS.

My most major question is, where do I go from here?

@William Jobe Do a flat fee MLS listing ($100-$200) so you get the same visibility as other listings (MLS + all major websites).

I would want some major security deposit on file - maybe 6 months rent (personally), and / or possibly have them carry an insurance policy with you as the named insured for a descent value for any damages, etc - with the policy specifically written for the type of business they are actually running.

@Stuart Udis totally agree, I just have a major drawback where I can't 1031 and will have to pay taxes so as of now I'm not in a position where selling makes sense, definitely in a couple of years.

I don't want to buy a house that need major roof work.   

The problem is it sucks, it barely works, it's surprisingly unintuitive for something so simple, and barely any guests actually use it.Which is kind of the same reason we're not discussing this on Google+ while wearing our Google glasses and talking about which version of Google Stadia is best to put into our homes as we communicate with our cleaners through Google Hangouts.While google obviously has a few big hits like Maps/Flights/Gmail, the majority of google releases follow the same pattern of great technology, horrible interface, no marketing, and eventual abandonment by Google.