The zoning is RS3, so we'd have to wait til ADUs are allowed city-wide + dig down to meet the ceiling height requirement if we want to make it a third legal unit which is not something that financially makes sense right now.  

That would require me to enter 100 Properties and set up rules for 100 properties, over setting up one property that passes its rules down to 100 units. 

In New York, depending on the deal of course, many properties require 25+% down payments in order to cashflow.

The down payment plus closing costs, expenses to make the property rent ready, travel back and forth (do not purchase a property in a market that you have not visited and/or do not plan to visit pre and post purchase), and the required cash reserves puts your realistic purchase price around $150k. 

@Sandy Keller many states require a lease to state the owner of the rental property and any property manager/agent for the owner.Check your state laws!

Is it possible to list a rental for single occupancy only? Or does that violate fair housing laws? I've seen limits of 2 people per bedroom, so I imagine I could limit it to one person per bedroom? Thanks for the advi...

For the purchase of the new property, you can consider a seller carry offer (balance of purchase price minus the down payment) or obtain a new mortgage on the commercial/resort. 

This would require incredibly expensive work as we would have to cut through a public street.

Therefore if the required hours are put in, then you may be able to use the losses to offset your non passive income such as W-2 wages.  

We require strong LL referrals and state this requires more than paying your rent on time.