Quote from @Diana Mulvihill: I think "soaking tub" is a more accurate term.

If you give them a shorter term lease, do it at a higher rent as you are going to be inconvenienced trying to find a new tenant at what may be a hard time of year. 

That's as long as you can afford to acquire it in the first place.The question you should ask yourself is if you want section 8 in the first place.

In any building that allows short term rentals, you will have a majority of the owners doing STR. 

Going this route over high closing costs would save you more money as long as the work can be done in reasonable amount of time.

First unit lease is up for renewal on 10/31/2024 and has a good long term tenant.

How are long term rentals doing?

I know that in Mississippi the rule of thumb seems to be that as long as the lot can meet the frontage requirements, construction is permitted.

Firstly, it's important to point out that Pismo Beach, like many other California towns, has imposed stricter regulations on STRs in recent times.The city has drawn a distinction between three types of authorized 'Less Than 30-Day Rentals,' specifically a "Short Term Rental," a "Vacation Rental," and a "Homestay Rental."

Total cost significantly below their current monthly rent.3- If you have to 'give them' to the current tenant to get them off your books then do if it makes sense long term.  4- Don't do purchase contracts longer than 18   months.