We are fully booked for high season (Dec-March) through 2026.I know this is not the typical investment, so totally appreciate any advice anyone may offer.

I tried using fb groups but they don't seem very effective.

Effectively, if you're asking about 2024, you'd be able to take the de minimis election for appliances and such you bought during 2024 but would need to capitalize 2023 and before.

These places will be more expensive, for a reason.Now I do think that there is some opportunity in certain areas of upstate NY for short term rentals, however upstate NY is not a well established travel destination so your occupancy will probably be low and highly seasonal but this method is viable.

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Yes, today with the high prices and high interest rates it is harder , but still not impossible.  

The easement must be evidenced by written instrument recorded in the office of the clerk of the circuit court in the county where such land is located before the recording of such tax deed or master’s deed, or, if not recorded, an easement for a public service purpose must be evidenced by wires, poles, or other visible occupation, an easement for drainage must be evidenced by a waterway, water bed, or other visible occupation, and an easement for the purpose of ingress and egress must be evidenced by a road or other visible occupation to be entitled to the benefit of this section; however, this shall apply only to tax deeds issued after the effective date of this act.197.573 Survival of restrictions and covenants after tax sale.—(1) When a deed or other recorded instrument in the chain of title contains restrictions and covenants running with the land, as hereinafter defined and limited, the restrictions and covenants shall survive and be enforceable after the issuance of a tax deed or master’s deed, or a clerk’s certificate of title upon foreclosure of a tax deed, tax certificate, or tax lien, to the same extent that it would be enforceable against a voluntary grantee of the owner of the title immediately before the delivery of the tax deed, master’s deed, or clerk’s certificate of title.

I think this tenant is starting to come across as high maintenance and this was just another thing piled on top of other things.Nearly every day she has asked me to do something. 

If it was my thing, ever high was in like new condition, and it fit the theme I was going for maybe I’d pay $5-$10k more for it to be setup?

It is very high chance that I will be negative cash flow due to increase property insurance and HOA.