If you are in an expensive state, having a separate LLC per property might be too expensive to justify unless the equity in a given property is sufficiently large.

I guess I am here because I feel lost and overwhelmed and want to learn how to make the most of this situation to achieve my goals in a safe way over the next 1-5 years if possible.

For those that had loss of use or ALE (alternative living expense) insurance, the insurance company was required to pay for your like-kind housing while you rebuild which includes furnishing the rental as well. 

I had a huge amount of expenses in 2022- pool, new windows and doors, that I was unable to use as deductions because of my W2 income.  

However building small unit count, small units is very expensive housing.  

PPC is getting quite competitive and expensive so I don't know how long it will last. 

Unless we note otherwise in the listing information or disclosures, we fix everything that is broken or not functioning properly, but we have had several recent requests that are expensive and I'm interested in your experience in handling things like:- this roof is old and we're worried that we may have to replace it (was inspected by roofer and determined to be functioning properly)- there are screens missing from some of the windows and we would like you to add them- we're concerned about the drainage and would like you to add gutters- the AC unit is old (age disclosed in disclosure docs, was tested by HVAC guy and running fine) So do you budget for this type of concession, do you "meet in the middle" or do something else?  

If you have equity in the property you need to deduct a 10% return off the top of the rent as a additional expense otherwise the equity is being wasted.

My understanding of a self-directed retirement account, though, will make it so that the income from the rental will have to go back into the account and we cannot use it as passive income for our normal personal expenses.  

This will decrease the amount of your out of pocket expenses.