My current employer has said that they want us back in the office eventually, but have not yet given us a set date. 

The cash generated in this is not taxable and can be used as you wish in the improvement of the new property.

Will require a lot of time and effort.The forums are generating a lot of buzz around STRs.

When you're a mortgage banker (inclusive of at credit unions) and your employer doesn't want more of Z type business, there's nothing you can do but turn away those customers until the employer gets hungry for Z again (or try to sell crappy loans, they b/c usually continue to offer Z-type loans, just with horrible rates/fees/terms).

So if your $25k loss is generated by depreciation you won't have an issue with lending4.

Investing in real estate would make me a third generation real estate investor in my family.

Every firm/brokerage is going to be different though (especially if you are on an employer plan) so you would need to do some research on that. 

Investing in Real Estate is an amazing tool to generate wealth, however NYC is certainly tough.

No need for landlord classes and if it's not rented, they won't give you credit for any income the property may generate.  

And it looks like we are heading into another unseasonably hot fall as ultra-low mortgage rates and employers’ remote-work policies mean Americans are still on the move.”Key housing market takeaways for 400+ U.S. metro areas:Unless otherwise noted, the data in this report covers the four-week period ending September 19.