I hope they've researched enough, some cities have the craziest regulations." haha and here you are backing him up!

Then there is Airbnb and all of the regulations that come with that, but I know people who have done really well. 

I don't have a lease with them (they've paid on time every month) and, as far as I'm aware, there isn't a written lease leftover from the previous owner (doesn't mean it doesn't exist, though). 

The one caveat about the STR market is that municipalities around the world are beginning to regulate the market so what is legal today might not be tomorrow.

These regulations seem to be changing daily.  

NYC is a highly competitive market and unpredictable with talk of more rent regulation and potential commercial rent regulation and sub 4% cap rates.

But if I were in your shoes I’d weigh a few different options.  1) you could refinance your existing property and pull out a bunch of cash and use that to pay for additional down payments. 2) 1031 exchange into a larger 5 plus unit. 3).

From what I've seen, the successful young commercial brokers partnered with seasoned realtors back in 2007/2008, and utilized their partner's existing network and knowledge to allow them to launch like a rocket ship after the crash.

2) What is the anticipated cash flow of the existing units, if leveraged at 80% LTV?

I am investigating the option to move a rental property from direct ownership to an existing LP.