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. 

Connecting with local real estate investors and getting advice from experts can help you understand market patterns and investment techniques.

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.

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

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. 

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

Make sure to connect with local lenders and brokers too.

Also, your small local banks may be a good options; however, they usually go into a 5/25 ARM products. 

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

300 or 400 would be ok for a smaller house.You can provide You Tube TV for cable and local channels so you don't look too cheap.