That being said, booking.com had a high occurrence of fraud so we no longer use them.

Is it worth investing in Manhattan given the high property values, tenant-friendly laws, and rent stabilization?

I highly recommend you get some help from a local investor or agent to help guide you through the process since this all new to you.

Basic your business model on short-term rental income is risky in that, over the 30 years, regulations can and do change (not to mention oversaturation resulting from the high interest rates pushing investors to rent short-term to try to get any sort of cash flow).We have the same situation in Canada (less the 30-year mortgages) and that's one of the main reasons, aside from profitability, why I invest overseas like in places like Mexico where there is unlikely to be regulations anytime soon, neither at the governmental nor at the HOA level.

I do understand if your W2 taxes are not high enough then this doesn’t matter but if someone is paying a lot in taxes BRRR or any house flipping strategy might also save on taxes. 

However the HOA is very high ~$500 and it scares me to think about possible vacancy & the whole process of renting a home out.

To help in your search:be sure to find an accountant who is willing to grow with you, and is not too high priced fee-wise.

I found several houses on the market with prices too high to sell.

It's highly possible she's just not in a financial position to be a home owner so you can continue to rent into the future (does the property cash flow?)

What turned me off was the extremely high pressure tactics of the person who calls you for the interview.