We were doing a loan for a 4 unit in a smallish town in Alabama.  

I found a house in upstate NY right by Lake Champlain in a really quiet town.

I bought a $35k lot in a great part of town that was zoned to build a duplex in Fall 2019.

What part of town?

We met with a local (onsite in DP) property manager while we were in town but his model is more focused on month+ rentals in the winter months.

(town, city, etc.)

If the town has ordinance against it someone might report it (tenant when you tell them to leave, neighbor, ...)

You could try sending her a small gift, a large invitation envelope with a Starbucks gift card inside, a handwritten letter offering to take her to the best place in town for dinner to discuss the property.

I have used several different inspectors here in town.

I have been thinking about buying a house in the towns I move to and when I leave rent it out.