If you can’t view her as an SO independent of her splitting the REI workload, that’s really your issue

My broker sent me a contact for an independent broker and suggested i use him as a mentor and give him the lead.  

Try an independent insurance agent in your area and discuss your situation with them.

Across the board, the most successful owners have nurtured relationships with local real estate brokers, property managers, home inspectors, and other professionals who can collectively assist them in making high-quality acquisitions.I'm not a fan of the "turn-key" trap of working with a single "one-stop-shop" company: You want a team of independent, best-in-class operators who are beholden only to you as their client.If you'd like, I'd be happy to put you in touch with some of the folks I know who are doing this today.

Each way has independent considerations that come into play.  

I think this'll go nationwide soon.One way I'd like to try and counter attitude changes against Airbnb / STR is by branding my property, creating a website and marketing it independently.

Not sure about Hawaii, but most states where I've dealt with HOAs, it's standard in the contract that you have a right to review the HOA docs and exit the contract within x days if you don't like them for any reason, and listings usually say, Independently Verify, so not a lawyer but don't think you have "a claim on the realtors insurance," especially as you said you know the area well and didn't think it was correct.   

My goals for investing in Milwaukee are to create cash flow, and forced equity, to help fuel and drive my pursuit to financial independence.

- If not, then I'm wondering if securing the HEL would diminsh my ability to finance the SFR's independently (ideally within the same timeline to close).I have a solid credit score and f/t income that is strong, but would like to streamline the process as much as possible.

My goal is to be financially independent in the next two to three years.