so those owners are pretty comfortable - no mortgage payment - and they don't need to sell, and they don't care where an investor "needs" the price to be to make money. 

Hey TimI feel truly blessed by your response.

Medford (North Boston) happens to be a low supply/high demand market so I absolutely need to get more comfortable with consistent rent increases but those increases need to be researched and in line with the market. 

I feel like I keep watching videos but don’t take actionStop watching the videos.

See what they feel about their ability to pay.  

It will include a compact bathroom, a tiny kitchen area, and a heater—just the essentials to make it comfortable for someone to stay in.

Because they will get defensive if they feel you are pressuring them.

The answer would be partially dependent on what are you looking to get out of it for rent and what type of risks are you comfortable with?

Just make sure you’re comfortable with the interest rate if going either route.  

I feel bad for the pitbulls, they need to go somewhere but the owners also need to be responsible with them and as long as you make that clear then you shouldn't have a problem.