In these markets, I would be worried about crime, activity of illegal immigrants, and such. 

And if not, what other suggestions would you have for getting the comps I need to accurately assess ARV on flips? 

I keep coming across posters asking for advice on how to “scale” their investment or business activities.  

I spent a decade in advertising, before founding and running a custom wood shop for another decade, so 'm pretty good at the self-promotion.I agree with you that the more gorilla approach would be most effective and that's actually what i've been doing – calling RE agents in my service area with active listings, introducing myself to property managers and leasing agents...To answer your question, I will have to handle the work myself for 6-12 months to build out the SOPs and field service management systems, but I have a lot of relationships for those looking to "do the work".I'll check out the meet up and would love to grab a cup of coffee, I'll shoot you an email.

The plan includes high-yield activities such as property flips and strategic acquisitions to provide liquidity and generate returns.

We had to make sure we sidestepped them and only added information to the correctly entered, active applications.

I would think that a property manager would be able to assess your specific unit, be able to determine what market rate is for the local area and the quality of the unit, what the market rate rate is for your specific unit, to suggest what your unit could rent for based on some improvements and have a sense of what rent increase would be tolerable by the tenants. 

We have over 10,000 landlords in Milwaukee and at least a couple thousand active investors at any point in time.6.)

I'm originally from BR and am fairly active there. we see a lot of inventory so also happy to chat offline about this

Just being active and visible in the areas you want to buy in can work wonders.