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 kept meaning to buy for a few years, but I’ve been simply overloaded with a startup.My current country prevents me from purchasing property (non-citizen), and doesn’t offer fixed rate mortgages - the floating rate is high rate at 7%, and has been about this the last 20 years.

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.

Unless you are planning a DST (not sure if SDIRA's can hold this type of investment) which is similar to high rate bond investing depending on the rate of returns. 

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

With prices as high as they are and income not keeping up I think more and more families will buy property together. 

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. 

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

I think the price is too high, but it works perfectly and doesn't require much thought.