Rehoboth is probably a little better than Bethany for the off season, because it has more year round residents and activity, but rentals are still pretty dead over the winter. 

Insurance claims are never fun and with being in an HOA certainly makes it a bit more complicated.  

2.How to run the hot tub without guests for a few winter months (avoid headaches)?

It will be interesting to see if this trend sticks around now that we are out of the winter slump and buyers are moving again. 

Less choices in the fall/winter, but then again, we're not worried about where to put the tv, or what color the carpet is :) 

Not sure the best way since in summer electric will  be higher and winter gas.Would we list those yearly amounts in the lease and just use the last fully occupied year?

But the monthly cash flow builds up quick and it’s fun to go out and get another with 20% down.

Use a consistent naming convention - ex. 2024.03.25 Home Depot3 Maintain proper records - Contracts, Settlement Statements, Agreements, Promissory Notes etc.Additionally, you can track income and expenses consistently, using software or spreadsheets.As you scale, if bookkeeping isn't fun for you, consider hiring a bookkeeper for a couple hundred bucks per month.

Now if you have a place that is short term say in summer and mid-term winter because you get a significantly higher rate in one season for STR that makes sense.  

North Carolina, as an example, is Non-Judicial--but has the fun quirk of ten day upset bid periods during foreclosure.