The bigger issue may be the frequency of visits, so unless it is on your way to work or something, you may be driving there alot (in the snow of course)...On hiring it out: It might be ideal is to find someone who already does the neighboring multiplexes (and does it well).

I found a potential property near by for a ridiculously low price that I would like to attempt a flip on but read that the property has some foundation / settling issues.

It's been 4 months and the tenant continues to complain about multiple issues that our previous tenants had no problem with.

If you go a couple months with no issues and you want then to stick around, you may consider encouraging them to get into a longer term lease for the stability.  

If you have issues please let me know.

The issue I see with another investor taking it over as a rental, is that it doesn't really cash flow at the price it is currently worth.

I think I can build the second unit for $50-60k, but what it will appraise at is the big issue, as there are no comparables in my area that I or my realtor could find.My last house the FHA appraisal came in $10k less than the offered price, so even if the rent income justifies fully a $300k or $350k mortgage, if the FHA appraisal doesn't agree, I am screwed, this time for a much bigger amount.Certainly the difference between $250k, $300k, or $350k is huge, one has no profit, the other $100k profit!

Bathrooms are small, but you will most likely run into hidden issues on floors and walls and if you are paying a GC who is paying a sub, the costs can creep up there.

Be friendly (kind-considerate-respectful), firm (be clear about your expectations and have the moxie to address issues as they arise), fair (comply with the law, no favoritism, appropriate response to the situation) , fast (quick to respond to maintenance requests and other tenant concerns), and flexible (when the situation warrants).

Main issue is it stays with the property.