You could easily find a long term room mate and charge them $1000 or more a month.

In your case depending on how big of a house you buy and many roommates you can handle you have the potential to live for free, minus utilities of course.

Currently living on the main floor with two roommate renters and will be renting out the basement unit, which opens out to the backyard.

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.

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.

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.

College Students - Roommate issues, excessive wear and tear, limited income, higher turnover.

This is a roommate/tenant situation.

I haven't investigated this as I don't invest in SFR's   would be to go ahead and build out an ADU or ADU-ish space but still rent the whole home as a unit,  and advertise/describe the home in a manner that might appeal to a tenant with an extended family or roommates.