Quote from @Don Bessette: I have a 30 plus year tenant that can not keep up with maintaining their unit, it is filthy inside and in desperate need of renovation, all systems are in good repair and I respond very quickly when issues are brought to my attention.It is also well below market rent, and they struggle to pay the current rate.Looking for suggestions on how to gently proceed with the notification to move. 

DSCR loans are used to finance the property once you have tenants in the units.

In 15 years of management and 20 years of investing, I've never had a break-in on a vacant or occupied unit.

I have a complex next to mine that has over a hundred units, some do very well some dont and you can point to their decor right away as a differentiator.

To find value on residential 1-4 unit properties you could ask your realtor to run comps or complete a CMA(Comparative Market Analysis) on a subject property once you find it.or you can find the value on your own.We use prop stream to run comps. 

Units are cheap and they just put a Starbucks in so there's got to be something growing there.North of Worcester ie. 

I know that my current cash flow is a result of the unit being my primary residence first, and that not all units will cash flow like this, but can't help the feeling that I should be expanding my rental portfolio over the years.

I despise units that are older where sound travels easily or also units that have either more units above and below.

Hope this helps and feel free to DM me if I can be of any assistance locally. 

Reach out me as I am a local Realtor and can assist you!