A fee-only financial planner or real estate-focused CPA can help structure the sale, financing, and new purchase in a tax-efficient way.Good luck!

Thank you for the welcome and it’s a pleasure to meet your acquaintance, yes I definitely plan on starting off small and building a solid team so when I am ready for multifamily units, I will have a strong structure 

However, I want to ensure I'm properly structuring deals, receiving legal and fair compensation. 

I really liked finding the probate houses there, which often have great structure and outdated paint/carpet.  

It might not need a full replacement if it's still doing its job—keeping the rain out and protecting the structure.

It depends on the structure but I agree with you.

As for a Home Owner Association (HOA), whether it needs to comply depends on its legal structure and tax status.

Is the lot flat and straight forward, or will it need tiering and piering to keep the house structurally sound?

That sentence sums it up. 

Also buying new properties could allow you to create the proper legal structure if you haven't already.