That kind of restriction just doesn’t work for someone like me.I’m trying to figure out if I might be missing something in how I’m approaching this or if others have insights or examples of towns that not only allow STRs but also have laws that offer enough flexibility to operate in the way I’m aiming for.Many towns technically permit STRs but impose restrictive rules like membership requirements, ownership duration limits, or rental day caps, making operations challenging.

To confirm my recommendation ask him for references at his current developments, I bet he won’t give you names and will make up an excuse!

If we face any headwinds, liquid investments go first so probably crypto but then you bet equities will get pressed.

Establishing a separate entity, such as an LLC, for your rental property business could provide more flexibility in claiming deductions associated with business-related assets like vehicles.

It isn't impossible but as @Jimmy Lieu mentioned, there is a steep learning curve.Depending on your liquidity, out-of-state buy & hold rentals could be your best bet if NYC investing is out of the picture.

Bacon is more yummy than a Christmas tree, but I bet I'm going to have a whole lot less regulation growing Christmas trees... however, before we even get to that, it's necessary to know that the inquiry is even about bacon v Christmas trees, rather than Bacon v grapes. 

@Andrew Grimmett If a seller is hesitant due to capital gains taxes, consider creative solutions: suggest an installment sale (seller financing) to spread tax liability over time, a 1031 exchange to defer taxes by reinvesting in another property, or a structured sale for flexible deferred payments.

Not sure what your time restrictions are but the fastest way to financial freedom and flexibility in real estate is creating a business out of it.

In my opinion, that is a riskier bet because you have to have a big pile of cash for contingencies.  

agree .. other wise its just the bottom feeders looking to take his equity from him  with couching it as a rescue.. his best bet it to sell if its owner occ the profit is tax free .. regroup and start over..