What type of professional would I consult to help me evaluate this?

As far as moisture in the basement, you should have a foundation contractor evaluate it.

I am now able to do the following easily with this application1.

I've purchased nicer units and they seem to break just as easily as the cheap ones.

You should be able to easily find investment options that are very likely to achieve better return than 3.5% over the long term.Good luck

My nature is being really process oriented and when things fall behind because of little details that could have been easily addressed it drives me up the wall. :) 

If I had them managed, that would easily add 10-15% to the expenses.I think if you actually itemize all of your costs, you will quickly find that a $250k duplex with rents only $2k a month to be a marginal deal, and a bad deal when you try and finance 100% of the deal.  

Since they all follow the same guidelines, and it was an unbiased 3rd party, there is significantly higher chance your refi numbers will come out closer to what was expected than just trusting Realtor opinions (after all - banks don't hire them for an unbiased evaluation of homes prior to lending). 

There are a LOT of members you can easily reach out to and do your additional homework on though @Mason Jenkins

Evaluate the potential cash flow of other deals that come your way and compare it to the cash flow you're making now.