Plan currently is to offer a six month lease when their current lease ends to have it end in summer, with the thought that at any point they would give me their notice of vacating hopefully with atleast 30-45 days to find a new tenant.

So enjoy it and be persistent, and patient.

Are they going to be on vacation?

As mentioned everyone's strategy is different, I'm risk adverse & enjoy liquidity.

One option is do a cash out refinance on your current home and use that money as a down payment and vacate the home to transition it into a rental. 

.: Since you can live anywhere, I would find a strong market that you would enjoy, then buy a big house or a multi-family that allows you to rent spaces out and gain experience.

So, I accepted modest appreciation (doesn't really look that modest since about 2020, honestly), and enjoyed a steady income. 

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."

If the answer to the last question is because they would rather stay at home and don't want to get a job or they have a job, but want to 'enjoy' their lifestyle and not be 'burdened' by bills, then it is time for them to grow up and move out.

We have one vacation rental in Florida and a long term rental in Louisiana.