Looking to add this to my portfolio in the next couple of years.

It's a common problem but there are entire books on commercial/portfolio type of lending.  

I've found a nice city that has an old couple selling there rental portfolio, each duplex they are selling is around 50,000 and they rent out from 1000 - 1300 dollars a month (both sides added together).

@Frank Costa just tell him that you are local investor seeking to expend your portfolio. mentioning that his complex at XYZ St could be a good fit , and that you are interested in talking to him if they would consider selling. leave your phone number and email.

I don't want to keep working for the next 10 to 15 years in an industry where my earning potential is already capped while we build our investment portfolio, I'm just not sure contracting is the right direction given what we have already and of course it is back breaking work. 

Yes talk to commercial/portfolio lenders and call small local banks and credit unions in your area.

The buyers interest and yours might be better served by talking to a local portfolio lender who is not bound by Fannies regs and can be more flexible.No comment on whether the appraisal was right or wrong.

I am also wondering, your buddy that gave you the advice, what does his real estate investment portfolio look like?

Based out of California, I have a construction company in Cleveland that does high-end flips, and I also renovate rental property to keep in our portfolio.

I’m in search of a new real estate agent that can help me add to my buy and hold portfolio.