Second: What insurance coverages are recommended if I elect to run as a short term rental? 

Should the Applicant elect to pay the Deposit to Hold with their application (prior to processing), the Deposit to Hold will be refunded in full within 14 days if they fail to qualify.Move-in RequirementsAfter approval and before occupancy will be granted, Prospective Tenant must supply all the required move-in funds, including the security deposit, first month’s rent, and any other additional deposits and fees.

@Matthew Egan you could speak to the president of the HOA and see what their stance is on STRs.

ST gains if we elect to sell the property.

Here is generally how the strategy plays out: when a sponsor acquires a property, performs a cost segregation study, and takes the bonus election, the portion of the property's value that is allocated to land improvements gets depreciated 100% in the same calendar year the property was purchased.

For example, the "land basis" is something you should have elected in 1988 and carried on your tax returns since then.  

I was somewhere around $100k/year when my CPA told me to elect my LLC as an s-corp. 

We may see a recession in the coming 24 months if the Fed hikes rates sharply to curb inflation (this has happened like clockwork 3 times in the past 30 years, each time with a different Fed president at the helm - they all follow the same practices, it is just a matter of timing & implementation), but due to demand and the strength of the housing market, we may see at most a stagnation in prices, not a decrease, and then the march will continue up for real estate.

This is a rural property and 2 homes, plus an ADU are permitted, and for complicated reasons, I don't think we're going to elect to subdivide. 

@Ashish AcharyaReading about a 5year phase out when changing election from C Corp to S Corp. once it’s an S Corp it’s a pass through entity.