As long as you're in a good location where you see the rents and values continuing to go up over time it'll be a homerun in 10-20 years if/when you decide to sell or refinance. 

Additionally, they don't have the time or resources to research and investigate Owners calling with questions on legality of property/building renovations or proposed changes.

Hey Becca, Antoine here (owner of FlipSystem and MartelTurnkey).

If you do decide to pursue buy and hold I’d recommend long term rentals because there’s less people involvement.

Should I firmly tell her what to do or just let her decide and go with the flow?

Property management (if we decide to hold onto the property)If I were to sell the lot, what would be a fair price for me, considering that I can subdivide it into 4 lots?

Kings County Housing Court is a dark and expensive place where the tenants/occupants/even squatters have more 'rights' than landlords/owners! 

A a county employee she didn’t pay in to social security and as a small business owner I paid very little.

Look for a location that has attractions beyond skiing, such as hiking, biking, or water sports.Rental management: You'll need to decide whether you want to manage the rental yourself or hire a property management company.

Another lending option you can use aside from DSCR is Bank Statement loan program since you are a business owner.