Where I live, NE Illinois, the only LGBT Community Center is at the Community College. Looking at their pride page, it's open to staff and students. There is a "local" PFLAG chapter, but they only meet monthly and the most recent was in December. Otherwise it's a trip to Chicago, Racine, or Evanston, all a little more than 45 minutes in light traffic, away. So they're not really a readily available resource.
How would someone start a local organization so that we can have some actual local people to talk to and/or mentor ?
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Support groups are not the same as resources. To start resources, gather information that can benefit trans folk, and compile it on your computer. Create a web site listing the information. It is much easier that it was 27 years ago when I began my own transition.
If you want to start a support group, you might want to find some sort of cafe where y'all can meet. Find a time when it will be somewhat quiet, so people need not yell to be heard. Then, find a way to let other trans people know when and where you plan to hold meetings.
I noticed you did not mention Milwaukee. There is probably some sort of support group and resource center there.