Even in the off-season - you can optimize visibility by setting competitive pricing, using high-quality photos, and enabling Instant Book with flexible policies.For older listings, try adjusting prices with dynamic tools, highlighting upgrades, and regularly updating your title, photos, or descriptions to stay fresh in search results.These tweaks can make a big difference!

Since tax bills are for entire parcels (typically, though not always) then it is highly unlikely that they somehow segregated the taxes for that small portion and paid it.

I would only do this if you can find a quality property manager.

The quicker you can take action on the high dollar value decsions the quicker you will be able to grow.For sure take the time to setup the right foundation, but keeping it simple and easy when you are getting going is a safe bet!

It the accessment is too high and the real estate taxes as a result are too high, the net will be less. 

Be sure to take high-quality photos, and if possible, request utility records that confirm separate billing for four units.

Our actual carriers used to be Secura, but they seem to be getting out of a lot of insurance lines or pricing so high as to have customers drop off, and we just moved policies in Nov. to Hanover Insurance. 

@Tomas Falcon highly recommend you chat with @Samuel Eddinger!

Assume my marginal income tax bracket is very high, and mortgage rate is 5.25%.

I don't know your specific market all that well but have you done some analysis on your ADR during the high season X your high season occupancy rate and determined whether taking lower priced slow season bookings vs letting your property stay vacant during the winter averages out in your favor?