Just got a phone call from a local fencing contractor telling me that he just finished installing a fence at one of my rentals. 

Nothing beats local knowledge though & speaking with boots on the ground. 

I hope to learn from the collective expertise of the members on BP and build a local team in Milwaukee. 

Michigan might be a bit easier to start with because you may have more knowledge about the local area and market trends, but starting there could potentially slow down your move to Florida.

You're in the right place to network, going to some local meetups could prove beneficial to learning about investment opportunities as well.

Make sure to connect with local lenders and brokers too.

she is beachwoodbuyshouses on ig. i'm in MA and she is my CPA. she specializes in RE and is also a VERY active investor herself. she's based in long island. you don't have to use someone local. 

What if you could discover these stories without digging through old records or talking to past owners or locals in the area?

If you are going to invest locally I would recommend house hacking.

House-hacking today often has to rely on much greater lifestyle sacrifice than what I personally did 10 years ago, and requires strategies that would make me uncomfortable like rent by the room, or using local laws that allow Short-Term rental only for owner-occupants.