Suggesting to them buying their house for a wholesale range offer or lower dependent on the extent of the rehab, then having a contract in place that gives them a percentage of the profit to help get them back on their feet, paying off debts etc.

#McCormickI have some Youtube videos (link in my profile) that will help with some of your questions and I'd be happy to have a call to help walk you through the market and what you should consider when looking here.

As for meeting local wholesalers, networking at meetups or even online could help you connect with the right people. 

We've rented out some of our best investment properties (New Construction/Turnkey) to Sec 8 residents, and the rent guarantee always helps in achieving consistent cash flow each month.

You might be surprised, but your rental properties have more in common with dividend-paying stocks than you think!

That'll help you figure out what direction to aim in before speaking with a bank to figure out how much you can qualify for. 

I would guess an older home might be more cost to insure?

In my experience apt. conversions from single family are more prone to noise transmission. 

Give sellers the space to make their decisions without rushing the process—trust takes time to build.Listen More, Talk Less: The best closers are the best listeners.

New York is hard to evict people and you'll end up spending more time and money doing it yourself.