Hello Ilya,Where are you looking at purchasing your 1st property.When converting a property from a single family to a multi family, you will need to check on the zoning requirements, depending on your location, not every location has zoning.As far as lending goes, it is far easier to finance a single family up to a quadplex, than financing 5 plus units, the DSCR Market for 5+ units is extremely low right now, and there are few if any lenders in that space.For financing 1-4 units, there are Millions of dollars chasing those loans, so you can easily obtain long term financing, at rates between 5-7%.Please reach out if you have a property identified, and I can help you with financing options.

I.e. what if one doesn't get along with the other-Any benefits to trying to officially convert it to a duplex with the city if it is zoned to allow MF?

@Shahaf MatityahuYou apparently checked with City Planning which zoning is part of, and they advised you it's for only 2 apartments.

This lack of sophistication with money leads many to avoid using credit at all and just continuing to operate within their comfort zone.

You are not buying anything for 10k UNLESS they need TOTAL reno of 75k or more and are in a war zone.

I took it as a red flag and moved on. 

@Katrina Dividina  you are experienced so hopefully this is just forum-splaining :) just make sure the zoning allows it...sober living is usually addressed individually in the code and has its own hoops.Banks are charging 7.9% now and probably up so I would want a deal on the rate from the owner--where is he going to get 8%??

Newton is one of the hottest area with top schools and strict zoning laws so it's rather worse...I would say Waltham and Burlington are the only areas that are less negative cash flow

I was able to purchase the property through a commercial loan, as residential financing is not supported by through commercial zoning.

Permitting, zoning, finance, etc.3.)