How would you pull permits if you can't do so yourself?  

Oh and dont think about STR's...Charlottesville, Waynesboro, Staunton, and Harrisonburg have been denying permits due to affordable long term rentals. 

Both require a postal permit so the saving is gobbled up fast.  

Buy it as a duplex, do all the permits, etc, necessary for it to legally be a 3-unit.

When you apply for a rental license do they look for un-permitted work?

As someone who recently completed my first fix-and-flip project, I can share a few challenges that took me by surprise:Navigating the local permitting process was more complex and time-consuming than I anticipated.

I recommend you talk to an attorney to avoid making a legal mistake that permits them to stay longer.

We are in the season where we are getting some deer hunters coming up which is good because the big employers in this town have been cutting back so there aren't as many temp workers up here, which affects our occupancy levels.

Mainly some horror stories surrounding what you mentioned (not sending payments to a 3rd party, and then the lender activating due-on-sale).I'm definitely interested in DSCR since it I'm also a travel medical worker and have gaps in work history (will have another one in November), which could make traditional financing tricky (proof of employment). 

If it's traveling workers, they won't care.