I want to know all the pain points.

Pets are a pain in the butt for a multi unit rental you are trying to keep clean and improve the reputation on. 

The first one will be miserable, the second one a pain, but after you'd done it five times it's really quick and easy.  

There are definitely options available, depending on your grandmother's condition and perhaps more importantly how big of a pain in the butt the City of Wilmington feels like being. 

I'm doing one right now that is on propane and its become such a pain in the butt that I should have just went with electric.

You just have to run the total numbers for the year:Year-long lease at $1200/month: $14,400 in revenueNighly rentals at $100/night, rented for 120 days per year: $12,000 in revenueFor me to do short term, the revenue would have to be much higher because it's so much more wear and tear on the unit, as well as pain in the butt coordinating with the people, showing them the unit, cleaning up after they leave, etc.

Evictions can be slow and a pain.  

I had to get the permit amended and submit that to the abatement office. big time pain in the ***. do it right the first time and everything always works out.so now on my current flip, I did it the right way.

Most lawyers will say they can complete a close, but in my limited experience, non-real estate lawyers are generally uninformed pains in the asses.

If you are doing large capital improvement it is a pain in the butt jumping on a plane to manage those.