Currently they are paying $700/month but houses on the same street are paying $900-950/month, so I was thinking about raising rents once their current lease expires.

Yesterday, a house even closer to mine but at only 5,004 sq ft listed for $1,700,000.  2 of those three homes are on my street (the most prominent/prestigious street in my city) and the other was on a side street just off from it. 

2) Are there already utilities at the street?

If you PM me the street or neighborhood I can give you a little more info on the area. 

@Jim C.There is enough illegal marijuana in Worcester that i would not worry about the kind of customers this will draw, they are already there, if anything if this is a dispensary it will bring in more affluent people who aren't willing to buy on the street.

I have book smarts and street smarts.

Until we can raise enough knowledge, street Cred and capital to get into the medium to large multi-family where commercial financing makes sense.

My thinking is if I cant sell this property then I need to forget about the other 20 houses on this street. 

Since it is 2 Duplexes located on 2 different streets I would want to know the numbers for each individually.  

She has the income, seems stable, and would likely be a long-term renter being that her job is right down the street.#2 choice looks risky to me.