Adding a garage w/ additional unit in Hyde Park. Approval likely?

[Kavi S.]

Hi!

I'm looking at places in the Hyde Park or Roslindale areas for owner-occupied buy and hold, and in the future I would like to rent out the whole place as I move on in life. One of the things I'd really love to have is a large garage for my projects, and I've been thinking I might just build one on the right property.

I'm really aiming for a 3-family, but I've seen some 2-family places sell that I would have liked. I'm wondering how likely it is that the zoning department would allow an addition of a 2-3 car garage with a small additional unit on top to turn a 2 unit to a 3 unit. Or, perhaps, extending the smallest unit of an existing 3-family into additional space over a garage. Is that something that you could just call the department and ask about? Has anyone done something similar, or been denied permission? Is this something that people would file the zoning/land use paperwork for during the due diligence period? Is it a good indicator if there's 3-family homes within the same neighborhood or street? 

Thanks for any insight!