Also (if you choose well), you are hiring a manager who has many more years of experience than you can ever hope to have, and will avoid rookie mistakes.The downside is that not everyone feels comfortable doing due diligence on sponsors.

If the only MFH options you're finding are in areas you're not comfortable with, it might be worth focusing on a duplex in a better neighborhood.Saving up for a larger property later is a valid approach too, but keep in mind that real estate tends to appreciate over time, and waiting might make it harder to enter the market later.

Trade some comfort for financial stability.Part of attaining financial success is being simultaneously optimistic and paranoid. 

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.

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. 

Some investors are comfortable buying for appreciation or with the expectation that rents will grow at a faster pace.

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