Howdy "s8nlovesme".....
Welcome to the fun hobby of radio scanning.
There are only a few digital systems operating in southeast Wisconsin at the moment. Waukesha County (Motorola), City of Watertown (M/A COM-EDACS), Ozaukee County (M/A COM-EDACS), City of Greenfield (Motorola) and Milwaukee County (Motorola) Trunked Radio Systems around and they are mostly analog. Ozaukee County has some digital (Which is "Pro-Voice"), but that is not monitorable with any scanners on the market. Milwaukee County has a new P25 Trunked Radio System up and running that will be entirely digital, but no main users yet (And that is not listed in your monitoring targets).
All the talkgroups for the 440th ANG UHF TRS down at Mitchell Field are actually digital format. In two plus years in monitoring the system, I have never heard an analog talkgroup.
For you though...rebanding might be an issue, however. It depends on which scanners will work on the new channel plan. Also, I am betting that soon (Within 5 years???) Waukesha County will decide that digital is the way to go.
Tim