The transfer tax within the city itself is fairly high as well so going just outside of the city would be a good place to start. 

People come to them because they know they will give them a fair price and solve their problems.

It's fairly rare to have a structure that varies on the amounts like that. 4-5% is reasonable. 

I was looking to buy a home from him last year but he blasted me in an email for looking him up on @biggerpockets  in this post, so I stopped communication. 

"assuming" 5% appreciation is fairly aggressive .. 

A lot of times there are some title issues with these types of properties that you'll have to clean up, but they are generally fairly easy to resolve.

It's a fairly easy switch to convert from STR to MTR.

I just read many people are leaving New York but besides COVID I feel the city is fairly recession proof (as is DC which is where I have another property but it hasn't really increased in value that much).

This raised some doubt and we communicated to our agent that we are not satisfied but she kept insisting “there’s nothing you can do” and “you went non contingent” Then later she sent an email saying we passed the 17 day inspection period which we didn’t know about.

Those are some great questions to ask and the clear communication up front is definitely key.