I am hoping to connect with both investors as well as Real Estate agents in this area to understand the market better ( I have lived elsewhere for the past 10 years) as well as what areas may make most sense and with what strategy. 

I feel myself leaning more and more towards becoming an agent.

Best of luck in Knoxville, not sure I have investors in that market that could help, but I do know a couple of agents that could provide some perspective. 

I just pulled out an old amortization book that Fidelity published and gave out to us new agents.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

It’s not because self-management hasn't worked, but rather because I’m looking to free up my time to scale my portfolio further and focus on some other time-intensive projects.If you’re managing from a distance, the key is building a local network you trust—contractors, handymen, leasing agents.

Talk with multiple agents, property managers, handymen, and contractors.

Hi there,Given the complexity of your situation—owning a rental property in Florida while residing in Illinois, house hacking with your daughter, and planning to claim tax breaks—it might be a good idea to consult with a Certified Public Accountant (CPA) or an Enrolled Agent (EA) who specializes in real estate taxation.While your current tax professional at HR Block has experience with multiple properties, a specialist can offer more in-depth knowledge on multi-state tax issues, rental income reporting, depreciation, and maximizing deductions specific to real estate investments.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

I'll bet my favorite Tulsa super-agent, @Tom O'Stasik, could answer your questions!