If there is nothing in our HOAs about short term rentals, do we still need to ask permission to start one?

D) If and when she says something to you, I'm sure a short "Sorry for your loss" is acceptable. 

Evictions can take several months under the best of circumstances, and we are going to be going into winter shortly.

Its already being rented short term with a 90% occupancy rate.

We have several dozen rental properties, flip a few houses per year and are just getting ready to add a new venture with a few short term Airbnb's.

Long or short?

The 3-5% FMV discount is normally super attractive but I'm worried that because of the incredibly high property values right now, we may be in for a correction in the next few years, wiping that discount out (at least in the short run).

That 45 days is very short and you may find that you have to buy something that might not have been your first choice.

This is the short hand way of how lenders underwrite MF so you should too.Figure out the average cap rate for the area and compare if you are over paying or found a good deal. 

Short of that, you can be nice and give him 30 days notice of termination of work agreement and 30 days notice to apply for his apartment, the same as similarly situated tenants.