And even though virtually every sponsor agreement allows me to share investment information with others who might be advising me on it (especially when club members are bound by an NDA), I still ask the sponsor if I can share it, because it's a test.

Being able to raise rents after the rehabs will sting at first (up front) but will definitely help moving forward with cashflow.as mentioned above, staggering leases could help mitigate. 

Let's talk to see if Milwaukee, WI and Raise the Standard Real Estate is a right fit for your goals.Beleza 

They already lost some major players due to the state capping rates https://www.foxbusiness.com/lifestyle/california-insurance-c... will all insurance companies stop coverage, raise rates or reduce what they cover?

But you should be raising rent $100-$200/month every year.

I am days/weeks away from trying it at my personal residence.  3500 sqft but only two people using it, so not sure how good of a test it will be. 

Why not test the market by putting the lots up for sale, and if nobody bites, that might provide your answer. 

My duplexes already at market rent and only exsecting 3% raises each year.

Nothing wrong with being an agent, but like others have said..an agent will have way more resources, credibility, for commercial real estate.If you raised money and portrayed yourself as a professional investment firm, kind of like a mini hedge fund, and networked with owners and professionals, and end up getting a deal because now you're  a real buyer with money, and you flip that property to another outfit or individual at a large mark-up..that's what I always considered wholesaling.The problem with all of this is, commercial owners are smart, commercial buyers are smart, very smart and will see through BS immediately.So a buyer may see what you're doing, but, if you got a really good deal, and it has re-positioning opportunity, value-adds, then they will buy. 

It's good to test things and see what works for you and what doesn't.