The BP podcast is awesome, read all the books you can get your hands on, and then after you're exhausted of reading and you feel like you know it, then move to the next step. 

Remember, the 20k is after the 163k rental income has been exhausted to pay for these properties.  

When you've exhausted all your other reasonable options?

I have exhaustively read IRC 4975 and related docs (even the IRS guidelines for auditors examining prohibited transaction violations), and I can't find anything to support what I was told by my custodian.

Just have this lingering thought that I could be doing more pre-LOI, but I've probably exhausted that analysis.

The risk/reward is great, but the headaches from constantly changing tenants and having to babysit the property manager/fire the property manager is exhausting. 

I'll attach some photos of the property pre-rehab.I could go into way more detail on the financing/rehab/furnishing side of things but I am exhausted from 2 months of painting and furniture assembling.

If you can't use all the benefits in year one of doing the study, you can always roll the benefits forward until they are exhausted.

I have exhausted my cash funds to purchase homes and will start doing HELOC/cash out refi to continue buying.  

You only need one umbrella policy, as the name implies, it is umbrella coverage for when all of your other coverage is exhausted.