You will love Madison if you are looking for those things... all pretty easy to find.
You'll probably want to live close to the Isthmus. Near east is generally more affordable than near west, but both have really nice, progressive neighborhoods. There's a couple of cohousing communities, too... Arboretum cohousing and Troy Gardens are two that come to mind.
Wildwood clinic is a great option for family practice, they take a lot of insurances and are on the east side.
We have many homebirth midwives in town: Ingrid Andersson www.gentlehomebirth.org
, Debbie Healy (and Britt Wanta just joined her as partner) www.openarmsmidwifery.com
and Leah Hatcher www.leahhatcherbabycatcher.com
are all WONDERFUL. I think it's just a matter of personality and philosophy connections.
I'll second Happy Bambino-- wonderful resource. Also, momsinmadison.com has a lot of resources listed. If you connect with the co-op and Happy Bambino, you'll find the path to a lot of stuff in town.
As for raw milk, Jordandal farms in a source lots of families use. It's in Argyle, so not close by. But I know some folks get together and carpool and/or have others pick up milk/cream/butter.