Mason,From an insurance perspective I would add, getting 5 year (or more if possible) Loss Runs. 

Since you have the cost segregation study to provide proof of the value of the roof separate from the building, you can easily write off the $450,000 loss.

We’d rather take low double digits passive with lower risk over 25-35% active with the risk of principal loss.

If you sit vacant for one month, that's a loss of $2800 (mortgage, utilities, lawn mowing, etc.) and it would take 35 months of $80 cash flow to earn it back.

Quote from @Kadia Lawrence: I won't accept new renters with section 8 because HUD delays are ridiculous and result in additional loss of income.

According to wealthability contact, our shares given to daughters will be considered passive income and therefore able to offset passive losses from rental investment in the future.my cpa does not do any of these planning for us and we paid a lot of taxes (especially after Biden).  

Here’s why:- unless you strategically reported your taxes as making 100% income and not reporting an entire loss on your schedule e - you will most likely not find a lender who will qualify you for a HELOC.

  - the other thing I worry about is people like unscrupulous wholesalers or RE people taking advantage of them in the aftermath of a loss.   

People can and do lose money in ETFs, go back and find the paragraph about the average investor loss in Fidelity Magellen fund back during Peter Lynch tenure.  

Do a tax loss harvest  4.