Get out of your comfort zone.

You can really pick where you want to be on the "comfortability to profitability" scale here where I felt like those options in most markets were limited. 3) it's a great place to live all-around.

Get out of your comfort zone.

I have STR investors in Florida making 25% cash on cash returns, long term rental investors picking up properties directly off the MLS and cash flowing day 1 in various states, and house hackers completely removing their housing payment from the picture allowing them to save for for the next property.The beautiful thing about real estate is there are so many ways to succeed and a plethora of strategies depending on your comfort level and how active you want to be.

You don’t have a large enough portfolio of houses for a lender to feel comfortable without a personal guarantee. 

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. 

So people fill comfortable.  

Get things in writing if you're not comfortable with what you see or hear.

It really comes down to what is your comfort level with debt?

So it's really what you are comfortable with and what your investment thesis is.