There's chipping paint on the foundation outside.

We could get a new car and do something fun with the money but that would just be wasting the equity we have built up...bad idea.  

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)? 

Don't ask, unless he just built all of this and it is fresh on his mind. 

Hello all! 
A little about me to frame the post.  I have been working in commercial construction for almost 6 years now.  Last year I bought my first single family rental (B- neighborhood) after about 5 years of list...

Having worked in commercial real estate for nearly 20 years, and knowing many people that have been at it for 30+ years:1) no one ever goes bankrupt with no debt2) Most everyone I know in their mid-50s or older, that have built large portfolios (with debt, admittedly), seem to move from acquisition mode to debt pay down mode.

I'm ready to sign an offer to purchase on a property that has water in the basement/foundation cracks. 

Now that I have the foundation I needed from the mini-course, I'll be doing most of the research on my own.

Purchased all cash as a major fire damaged home & knocked almost all of it down and re-built it with new addition and rooftop deck with jet-liner views of the city!

These options allow them to control expenses better, attract similar tenants, and often achieve higher rents with lower costs.I believe there is a promising market for purpose-built attached single-family homes for rent in Worcester.