The reason your hard money lender is a good second opinion is because his money is riding on the deal.

Where in NY do you hail from?

Just ride it out the usual 30 year mortgage based on a positive cashflow model.

Ive never bought in Brewerytown but ride through there weekly and have friends that live/work there. 

.; divorced, teens exiting foster care (18-21 age). yes there is a need. you need to know where your clients will hail from. there you will find them at DHS/DSS/WIC/DV/ agencies. single rooms, shared kitchen, bath etc. all very commonly used for "temporary/shelter care" housing. for 30days to one year. pending --usual things like court hearings, sentencings, adjudications, or pending finding a larger unit to reunify with children taken by CPS. be ready for drama. but if you work it hard-the state/county/federal will pay.

Then I also had a very low wind/hail deductible (basically the roof).

I was big into snowboarding and riding sport bikes. 

Hammond is a great rental market and an easy ride from Chicago.

@Dylan FellowsI've owned 2 duplexes near there -  mine were in Cherry Creek -- so Harry/Rock just a hair south of Harry and E of Rock - virtually same area -- decent area of town - rent is affordable and you're spot on with the rent estimates -- $895-995 would likely be most reasonable - maybe $1100 if you decked out the unit and it was super nice 3/2Anyways one thing to be careful of in that part of town is the basements -- I had one of mine flood a bit due to poor drainage -- that can happen anywhere but there is a lot of clay in that part of town - So look for any bowing walls, stay on top of your drainage and you'll be good - downspouts draining away from the house - bury them if you need to - stay on top of the sump pump, clean the gutters etc  and make sure the ground slopes away from the house.Looking at comparable rentals on Zillow or hotpads or Facebook marketplace is a good place to run your own comps -- I dont use the rent-meter site - I dont trust it - but I guess it can give you an idea.Most of the houses should have had their roofs replaced in that part of town as around 2010 - 2013 or so - somewhere in that time and area various  hail storms and a tornado/windstorm went through.  

Buy low and ride the appreciation.