It wouldn't hurt to make some phone calls and see what type of a response you get on how the city feels about STR. 

Personally I'm not a fan of getting pressured into a deal - if you don't feel good about rushing into the deal, it's better to back out.

Many people are in all kinds of situation where some quick cash is way more important than hold on to a destress property that's not doing anything for them but causing pain. 3.

Feel free to answer any other questions I should be ask but not smart enough to realize it 😀

Feel free to shoot me a DM and I will make the introduction. 

If you ever have any questions, feel free to reach out.

If the property is listed on Airbnb/VRBO it will be hard to transfer reservations and that could be a huge pain if the seller is not helpful, even after closing. 

I feel those that were doing it for kindness was also doing it with naivety; they probably never foresaw a case where their kindness would make it difficult to sell their property at comp value.when rent control passes, rents go up.  

If you need help running numbers to determine the return of both options, or simply chat further feel free to reach out.

I was thinking of sending them a PDF flyer of something along the lines of "How to screen a tenant", "First time homeowners must do for the first 60 days", "what to expect from your first multi-family property", but i feel that might be a bit to simple.