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.

Taking your general contractor to the property is a must but getting a paid independent inspector is one of the best investments that you can make before you pull the trigger and purchase a property with hidden surprises that will empty your wallet.3) Budget ObsessionsThe third most important tip for successful flipping comes from the art of budgeting.

Typically, they work for itty-bitty independent agencies, if for anyone.

Are all units located on one lot or multiple/independent lots?  

I have done a decent amount of independent reading and learning but that only goes so far.