This was my first property, and while it's been a great learning experience, I made several mistakes along the way—ranging from choosing a realtor who was more focused on closing the deal than finding the right house, to having a poor inspection and overlooking issues hidden beneath the surface (literally).

Then you have someone who understands the investors goals well and the technical experts really working together effectively. 

Quote from @Shakthi Kamal: If you don't know the answer, choose the umbrella insurance.

Lets start with the goal.

What's most important is what aligns with your goals and your investment thesis?

However, due to rising insurance and tax costs, I'm starting to feel the financial pinch as the tenant currently pays rent 60% below the market average.My long-term goal is to acquire more properties, and I've considered doing a cash-out refinance to access equity for reinvestment.

Don’t hesitate to ask questions, share your goals, or contribute to discussions.

With high price per door and high rates, you wont find any cash flow.STR market is also very saturated and we're seeing more regulation there.I'd keep the end goal bigger multifamily deals.

Long term goal is to continue building my portfolio of investment properties. 

Now some choose to do it with TK companies and give up the control factor that you have with your investments.