I would stay away from owning a primary residence with multiple family members, it tends to get really hairy down the road, but owning an investment property with family members is less hairy. 

Areas tend to get blocked when a driver gets robbed or something of the sort.

A strict HOA is probably more likely to cite you for HOA violations, as tenants tend to care less about the condo that they're living in than a homeowner would. 

You're generally seeing $150-$200/door unless you do a really strong BRRRR and pull out most/all of your capital (then it tends to be less). 

As mentioned above, S8 properties tend to be in bad locations.

If you think rates will be consistent for the next couple of years and you'll have consistent deal flow to use the funds I would tend towards doing a cash-out refi on the existing property that you own free and clear. 

Hobby landlords tend to approach all aspects of the business from the perspective of doing as little work as absolutely possible in return forfeiting the higher profits. 

This assumes ~8% interest rates.Interest rates in New York tend to be 25-50 points higher than the national average although maybe I suck at finding good mortgage brokers.

A low rate doesn't mean much if you can't rent out the unit, and HOA fees tend to increase over time.

Financing options: I know local Canadian bank tend to be more conservative and not beneficial when it comes to investment properties in the U.S. so I'd be happy to assist.