I don't know much about homeschooling, since my dd is 8 mo. One of the women from my birth class homeschools her 11yo and I recall her saying there was pretty decent support.
I live in Springfield just across the Willamette River from Eugene, a town which most Eugenians classify as more redneck, backward and religious. But after 10 years of living in our cute downtown historic district neighborhood, I have to say I love Spfd better than Eug and it's plenty crunchy on this side of the river and frankly I find the majority of folks in Spfd to be more liberal and open-minded than Eug- I think Eug can sometimes be a bit snobby. That said, as Dani76 says, parts of Eugene are better than others and it is nice out where she is. Also, Moon Mountain, Riverview neighborhood is pretty good too.
I see plenty of babes being worn and I've yet to have anyone bat an eye when I talk about cosleeping with our dd. And that's at the Fred Meyer Grocery here in Spfd.
There are a lot of alternative care providers in the Eug/Spfd area and naturopaths, homeopaths, accupuncture, cranial-sacral therapy... I like Wynant's Health Foods for a health food store, especially since they're walking distance from my house, but there are quite a few good local markets (Capellas, Sundance, Kiva) and the farmers markets are great (they usually run clear into October because of our normally mild weather). There are plenty of gluten-frees, vegans, etc., etc. around here. Oregon also has the misfortune to have a higher than average rate of autism, so, although I have no firsthand experience, I believe there is a good amount of support/help available.
I think Spfd has the advantage over Eugene for living costs too. Rent and mortgages tend to be cheaper in Spfd and property taxes (if you plan to buy/own) and utilities are less too. Rents are probably a little higher than they should be, probably because it's also a college town (UofO). I second Dani's recommend on Craigslist.
Meeting people- that's hard anywhere. It's taken me this long to form friendships however I'm rather reserved and slow at that anyway. I don't personally know many moms w/ babies or young ones tho. I was actually thinking about going to one of the LLL meetings and/or was going to post here to see who's out there. (Hi Dani76!, maybe we should chat...)
I hope you find what you need and wish you the best of luck