Once you have family and get a bit older, house hacking gets difficult. 

It sounds like the 2 BR floor plan makes this process even more difficult.

., Purchase Price: $475,000 ($197.9/sq. ft.).Estimated Market Value: $402,000 ($168/sq. ft.).Financing Terms: 2% interest rate, with a 9-year balloon.Unit B Income: $2,049/month (Section 8 tenant through November 2025).Unit A Income Potential: Similar rent or higher; Section 8 cap for the area is $3,234/month.Monthly Loan Payment (P+I): $1,386.Cash Flow Breakdown (if both units are rented at $2,049/month):Gross Rent: $4,098/month.Vacancy (10%): $410/month.Operating Expenses (37.3%): $1,376/month.Net Cash Flow: $943/month.Key QuestionsWould you be comfortable paying an 18% premium for financing at 2%, especially in a market where current mortgage rates are closer to 7%?

I really don’t know how to move forward.I do not see how this works$3800 (rent) - ~$1600 (p&i) -$340 (taxes) - $250 (insurance) - ~$1200 (maintenace/cap ex) - $380 (PM)  - $180 (vacancy) - $400 (water) ~$50 (misc) = -$600/monthin a market that appreciation and rent growth has not historically kept up with inflation.  

Finding a good account and bookkeeper wasn't difficult and using online registered agents was way more cost effective.

Seems rather suspect with a 36% cap rate, and it's imperative to factor in the debt especially in a indefinitely and new normal high debt world.

My only concern to look out for is that things can go 'rural' pretty quickly if you start venturing outside of town, and most lenders are going to put the brakes on financing if the appraisal lists the property as 'rural' (has to do with what they perceive as the availability of future tenants).Watertown, NY - It probably is as good as you believe, but the lending licensing is pretty tricky up there, so its just  bit more difficult to find lenders that operate up there.

It is not very difficult or complicated to evaluate commercial real estate, there are plenty of good books available that can teach you how, textbooks, online courses, community college classes, even excellent youtube videos etc, and it is actually quite enjoyable in the process to learn.

Of course, live wherever you want, if you see that storms are becoming difficult, it is easier to sell one home and move.

As you might already know, house prices in New York are extremely high, which makes it financially difficult for me to try house hacking here at the moment.