For older demographics, consider the availability of medical centers, entertainment, and restaurants.Buildings/Permits: Assess the city's growth compared to previous years.Determine if the city can accommodate future supply.Government Regulations: Examine the city's efforts and the type of businesses they are targeting.

If they decide to renew/extend, you can/should accommodate them by just rolling the Purchase Option payment and rent credits forward but sign new paperwork, new floor price, new mo rent credit.Take $1 for security deposit so it is a separate transaction and security deposit not confused by a tenant with the cost of the Purchase Option contract. 

They need to vacate and it is up to them to find other accommodations. 

Our policies clearly state 4 PM check in, and I couldn't accommodate an early check in anyway because the previous guests were still there and had until 10 AM to check out, then the house needed cleaning.

Luckily they have been accommodating and wanting the updates and willing to pay more for those... so far.

Permits required unless zoned for accommodations.  

Those with cash have a lot more choice as cap rates are starting to sloooooowly climb to accommodate the higher interest rates.BTW - There are several ways you can act as a cash investor without having to take a hit on the sales by not replacing mortgages. 

I have quite a few clients who self manage their vacation rentals from the mainland.Here is info directly off state of Hawaii website pertaining to vacation rentals (bold in mine):  If you’re off-island, you’ll need to designate a local contact who resides on the same island as the transient accommodation.

Let them know your trying to accommodate them and get everything fixed asap.

Sure, it may be zoned for an ADU, but does it have the lot size to accommodate an ADU to meet the setback requirements?