The issue is typically when there are multiple leases and it looks like rent by the room.

I am no stranger to critter issues. 

While they were a few minor incidents, like the tenant refusing entry to the appraiser due to COVID concerns or issues with fixing things that showed up in the inspection, Eric helped sort it all out in the end, and we got them resolved.

A lot of vacation towns will have houses zoned for commercial use, which will most likely protect you from any regulation issues if they want to say its a commercial use since you will already have the zoning for it.

Make sure the driveway/lot/street drainage does not go into your front door or garage, many do.Be aware that many houses started as Summer cabins in the 1950's and were added on and added on without permits or any building skill. 

Navigating appliance issues in a rental can be tricky, especially with a long-term, reliable tenant like yours.

Most are fine with that, but a few will have problems with it and claim there are legal issues, etc..

Collections, payables, marketing, maintenance, they are work great but with some small issues here and there.

If you are a real estate professional, you may potentially be able to buy some rental properties, perform cost segregation studies and eliminate the taxable income.The issue, is in a couple more years, your PM company will likely be more profitable and you will have rental proprties with reduced depreciation, further increasing your tax burden.

Looking at your lease terms compared to what I see on the ground during inspections:1) The big issue is where the cord goes.