My wife and I also invest in STRs and I spend a lot of time working over the best place to buy our next property.I've been looking at Packwood recently for a client.  

Westchester, although one of the hottest markets, has a ton of upside with opportunities for both cash-flow and equity. 2-4 family properties in Westchester are the 2nd most affordable in the NYC Metropolitan area (next to Suffolk County) making it easier to find cashflow opportunities when compared to the boroughs and other suburbs like Nassau.A client of ours in Westchester recently purchased a < $800K 2-family with a detached 3-car garage which brings in additional rental income - from a local business owner with commercial vehicles.

I'm not a typical Realtor perse looking for clients so I don't need the trust factor that may go with the REALTOR symbol in my marketing or anything.

Disallowed losses under wash sale rules increase the cost basis of replacement securities, potentially reducing future taxable gains.This post does not create a CPA-Client relationship.

Last thing to look at (and right out of the pages of our client's own experiences) might be starting a transition of wealth in the form of using 1031 strategically to purchase property that your heirs live in until you pass and they inherit. 

LLC offers no tax savings.This post does not create a CPA-Client relationship.

We've successfully delivered over 550 investment properties to over 180 clients worldwide following this process, and:Over 90% of clients have invested with us repeatedly, showing they are happy with their investments.Our average tenant stays over five years.2008 crash - Zero decline in rent and zero vacancies.COVID - Almost no impactEviction moratorium - Almost no impactFrom 2013 through 2023, the annual appreciation and rent growth rates were over 10% and 8%, respectively.Jonathan, I hope this helps.

Cost segregation is best for long-term holds and should be carefully planned with a CPA to align with your broader tax strategy.This post does not create a CPA-Client relationship.

I don't want to mess up with my first clients.... 

I’m sure this will get their attention.I had to do this same thing with a client that had not heard from the short term PM in months