The tenant is going from annual to month to month as of November 1st possibly anticipating it anyway.Quote from @Jonathan Greene: Listen to an old episode of the BP main podcast with Dion McNeely.

I do like real estate, I have a great eye for design, but would hate to have to evict someone—that would be my worst nightmare, so I’m not sure I’m cut out for being a landlord (although I would fully anticipate having a property manager)Is option #3 a far inferior option compared to keeping our expensive house in expensive city as a rental and only having to deal with one property that gives us great appreciation in 10 years ?

InvestorShort Term Rental HostMid Term Rental HostReal Estate AgentFix & FlipsNew ConstructionThe majority of my focus is south of Lexington in anticipation of a large mega site coming to the area. 

I am also anticipating more appreciation in next 5 years due to the Home's proximity to NYC.

We are seeking investment in this area as it is near family and our anticipated retirement. 

I anticipate that we will continue to experience housing shortages in 20 years due to population growth.Ultimately, anyone who buys multifamily today and holds on will experience a great deal of generational wealth. 

This using a machine learning approach creating returned something a little different than I first anticipated.

As we look towards 2025, experts anticipate that median home prices will remain below the national average [2].

However, this seems unlikely given the current high interest rates.I don't anticipate significant interest rate fluctuations for the next 6 to 9 months.

And I'm guessing that you're anticipating a jump back into the market after a correction.