Looking for guidance on the best way to proceed going forward in terms of asset protection and how to structure all of this real estate… 

It  depends on your risk tolerance and what other assets you’d like to protect.

Here's a blog I wrote about H.S.A.s invested in alternative assets Financial Independence Retire Early - Achieve FIRE Faster with a Self-Directed HSA- https://udirectira.com/achieve-fire-faster-with-a-self-direc...

At the current scenario, without knowing anything about you or your properties I will recommend either to look at a loan from your assets using DSCR loan.

A good real estate accountant can save you thousands of dollars by leveraging entity selection and formation, tax deductions, cost segregations, bonus depreciation and tax planning.I recommend finding an accountant specializing in real estate taxation, business taxation, financial planning and tax planning.Consider working with your accountant remotely to expand your options.I would also recommend looking for an accountant willing to work with you throughout the year.

Even though I wasn't a good asset manager, I made money on my properties. 

Real-life reps, to me, means seeing properties in person, whatever your asset class. 

The best ideas are the ones that make financial sense.One opinion...hope this helps (and that you're warm in this crazy weather we're having here in Florida).Best.

Yes, You can buy and asset, fix it up and rent it out to make money without you physically having to work for the money. 

If you are using it to buy a turnkey property which needs to produce cash flow to be considered a viable deal how does buying turnkey(Little to no cash flow) combined with HML(High interest only debt) make alot of sense financially?