Would you take a cut on the backend assuming a sale of the property after a year and it has been cashflowing? 

Buy a property as soon as you can.

A business minor could give you a good foundation in finance, management, and entrepreneurship, which could be useful in understanding cash flow and scaling your portfolio.

It might help to connect with local property managers who handle STRs to get a sense of what types of properties perform best. 

Are the leases even valid, if they are not signed by you or your property manager? 

Hey Jason,Sounds like it is time for you to refinance your properties into DSCR loans.

If there are any NY market stats/comparisons, you'd like to see in the future, post a reply or shoot me a PM.Below is a quick Q3 comparison between this year and '23 for Suffolk County:Summary:- Single Family values continue climbing- Multifamily Properties are selling faster than last year - Market activity (sold properties) has remained steadyMultifamily sale prices have (slightly) dropped despite sales activity remaining similar to Q3 last year.

Or buying a property in a seller's market, and then buying another one a few years later in a buyer's market.

I have a rental property.

Joining local real estate investment groups can be a great way to meet like-minded individuals and learn from their experiences.Start Small: Consider beginning with a single-family rental or a small multifamily property.