The property has 7 acres with a 3/2 main house and a second separate 2/1 house (which also needs renovation) with its own drive.  

I could easily train virtual assistants to handle these payments and have an app created for encrypting sensitive data for facilitating the transactions through financial service partners from my main line of business.

If so and the monthly payment isn't too bad then you're still moving the needle forward if your main goal is wealth generation and not just cash flow. 

I am located in Maine and have 2 six unit buildings, 2 four units, and a 5 unit. 

Keep in mind the 3 main ways you make money (cash-flow, mortgage pay-down, and market appreciation). 4.

We were able to buy low in a good neighborhood since the home was in need of some work, mainly needing cosmetic work and some deferred maintenance.

On the other hand, I feel one of the main advantages of passive investments (via syndication/crowdfunding) is that I can hire a manager who has years more experience than I can ever hope to obtain myself.

I got to my current financial success through a series of well thought out endeavors but with a massive sink or swim element as I am often self guided..."

If one or more units are vacant, the remaining units often don’t provide enough cash flow to cover expenses, making it harder to meet operating costs.Maintenance costs: A fourplex comes with four times the appliances, plumbing, HVAC systems, and other components to maintain, leading to significantly higher repair and maintenance expenses than single-family homes.If you want to see the detailed calculation, read this BP blog - More Units Doesn’t Mean More Money—Why a Single-Family Home Can Beat a Fourplex.Resale value: Multi-family properties have a limited buyer pool—mainly investors—who base their offers on CAP rates.

Example: owner bought $1 million SFH in San Francisco as primary, built 400 sq fit ADU, lives in ADU is making gross rental income STR  renting out two levels of main house, grosses $13,000 month.