Get out of your comfort zone.

If you’re working with VA-savvy lenders who are comfortable with your plan and don’t impose stricter rules, you might be able to rinse and repeat as you described.

Get out of your comfort zone.

I don't think it is a bad idea to find work in real estate somehow as it will allow you to be comfortable with being around it in general, such as a property management company.

The owners became friends with the tenants and do not feel comfortable raising rents on their friends. 

Quote from @Paul Azad: Beautiful property Blake, and great growing area, i drove through a few years ago, amazing scenerey and perrenial vacation spot, would you feel comfortable sharing the structure of the syndication for the investors, fees, projected IRR, or time weighted avg returns etc from a potential passive investor perspective?

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.

It really depends on the investor, their comfort level and goals. 

Get out of your comfort zone.

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