But usually for a tenant occupied it's like $90-120 per monthI've noticed a lot of multi-family buildings are pre-WWII housing inventory - are there restrictions or issues common with that (historic districts, crazy high utility costs, etc)?

I had a similar off-season challenge and decided to allow pets ( with restrictions and clear house rules) and I gave a 30% discount to try & attract  snowbirds ( I’m in FL) - my calendar filled up for a few  months with a few pet owner bookings and  2 separate 45 night bookings,  did all this on pricelabs & airbnb -best of luck ! 

But the neighbors told me when they built their house from ground 6 years ago, there was no issues for any building materials or trucks going through the alley. 3. the house is in historic district of Charlotte, meaning there are quite some restrictions on the exterior renovation. 

Same goes with restrictions on equipment.

One was the steps were a few inches off of code in height, and the railing broke when the guy fell. 

The city just passed a very confusing zoning regulation restricting student housing to a specific area, and we're all trying to figure out what the fallout will be.

Realtors often claim they're restricted to Realtor use, but that is incorrect. 

Also, make sure there aren't additional restrictions on the property condition, compared to a conventional loan. 

I called the HOA before I first bought the property to inquire about their rental restrictions.

There may be some restrictions on rentals in some of the MH parks, buying the MH's outright might be better than financing because there are some lending restrictions on older MH's.