Boston in particular is a strong market with great appreciation, a great tenant pool, and rents being as insane as they are it's nearly impossible not to pay less when you house hack vs. rent. 

I was also considering the REI expo in February so maybe I'll see you there.You're a self-proclaimed novice but I think many other members of the community would agree that you're well on your way given your potential cashflowing rental and equity.You seem to have a strong position which would allow you to keep growing your portfolio in the next few years.I'd recommend diversifying your RE portfolio the same way you're diversifying with other investments (REITs, Stocks, bonds etc.).

It is entirely possible to self-manage with a strong cleaning team.

Unlikely.The backup plan is to have a strong lease.

My hope is to build a strong network of like minded investors and real estate professionals that share similar goals, values, and experiences to help achieve successful REI deals!

I would consider selling, i’m not necessarily saying you should, BUT only hold if you have a very strong belief in the appreciation of this property. 

Hypothetically, if I found a property with strong rental demand, the income could cover loan payments, operating expenses, and generate a modest positive cash flow.While this example involves upfront risks, the idea would be to leverage my father’s expertise as a contractor to minimize renovation costs, boost the property’s value, and create a long-term asset that appreciates over time.

Even with a great opportunity, trust is the foundation of any partnership.In my partnership, we had already worked together on multiple deals—me as the agent and him as the investor buyer—so we had established a strong foundation of trust.

Your financial position is strong, and leveraging financing for your next rental while maintaining a conservative debt-to-income ratio is a smart approach—consider consulting a lender to explore options that align with your goals and keep your investments sustainable.

I like Clarksville, TN because of the strong fundamentals, minimal volatility, and balance of cash flow and appreciation opportunities.