At first I thought it was going to be miserable,  but then I found a couple of roommates. 

If he buys the house and rents to roommates and doesn't apply for rooming units, he might have problems with the township or with evicting non-paying tenants in court.

The plan is to live in the house with roommates, likely people I know.

While you can legally have 1 non-immediate family member roommate in a co-op in NYC, the bylaws of most co-ops will require any tenants will need board approval to move-in.

How is it biased that if you can score a property in Downtown or Midtown you will rent to roommates with a household income of 85k to 125k who are accountants or medical residents and the property costs less than 150k for a triplex that a unit rents for $1500, versus renting out a 4 bedroom home in Sterling Heights to a Husband and Wife with two kids that make 90K where the husband works for a roofing company the wife is a bartender, and the property cost 120k rents for 1600/mo.Those are real numbers out the portfolio.

You will be able to buy a decent sized house for the price range you mentioned and you wont be crowded together as much especially if you are planning to have 3 roommates.

In NYC its important to  be mindful of NYC Roommate Law which limits the amount of unrelated roommates that can occupy a unit - https://www.brickunderground.c...

I know when we were looking for rentals (private landlords only), they refused to allow us to have roommates due to the unrelated tenants law, as they were unwilling to take on that risk.

I could find a place near Johns Hopkins University, live there myself with another 1-2 roommates, and when I leave a year later, I can continue to rent it out as essentially student housing by swapping out one tenant at a time.

I think you need to run numbers on as many deals as possible(including having roommates in a SFR that you buy), find out what makes the most financial sense in your area, and then try to align each investment with your goals for the quality of life you are seeking and pick whichever works best.