I recently started checking out these forums and was delighted to find a note about Uruguay. I'm an American currently living in Montevideo with my Canadian husband and American/Canadian 2.5-year-old daughter. We moved here from San Francisco, California, nearly a year ago-- mainly just for the adventure of it and for a life más tranquila. It took us a while to settle in (find a place to rent that we liked and so forth), but now we love it.
To answer some of your questions:
Education: DD goes to a part-time (four hours in the afternoon) private daycare/preschool, which has worked out wonderfully. Her Spanish is probably better than mine now! It was easy to find a place that we liked-- they're all over the place, and there were no crazy waiting lists like there are in San Francisco. As far as I can tell, the style of her place is similar to most traditional daycares in the U.S. The price is a huge bargain for us: approx. US $150/month (compared to around $1,000 in SF). There are also free public preschools. There are lots of education options here, both public and private. I've heard the public schools are decent (although another expat whose kids attended one told me they valued conformity and mediocrity over individualism). I'm not sure if there are Montessori schools-- probably-- but I recently discovered that there's a Waldorf school. I'd love to send our daughter there, but it's way across town (we don't have a car, and it would be nearly an hour by bus each way) and she loves her current place anyway (which is just two blocks from our apartment).
Childcare solutions: Abundant, good, and affordable. Besides daycare/preschool, there are lots of excellent nannies and housekeepers here, charging from around US $3.50 to probably $7 per hour.
Healthcare: Very good, affordable, but yes, I believe it's generally quite medical on the childbirth front. However, I've been seeing more articles about natural childbirth in some of those mama and baby magazines here, which is encouraging. I've heard through the grapevine of one expat who recently had a homebirth. A friend of mine delivered her baby here naturally at one of the good private hospitals, Española. She told me it is designated a baby-friendly hospital, actually, and they were very helpful with breastfeeding and such. My family belongs to another private hospital, and we've been happy with it for overall health issues (in fact, DD was hospitalized twice over the winter due to bronchial spasms, which are apparently common here in the winter, but that's another story). Even there, though, my gut feeling is that they overprescribe stuff in general. And although I like DD's pediatrician, every time we go in for a check-up, she asks if I've finally weaned (I haven't, but I'm just going to lie next time because I'm tired of the question...she said that if I feel the need to keep nursing, I should have another baby...annoying). However, none of this is really any different than what we'd probably experience in an American hospital. And given all that, all three of us are fully covered through our hospital "scheme" for around US $320/month, which covers EVERYTHING (never once saw a bill or had to sign anything after those hospital stays).
Job situation: Yes, it would probably be hard to find work locally, and the pay would be low. I know some expats who teach. Your Spanish would probably need to be fluent. If you're the entrepreneurial type, though, there would likely be plenty of opportunities, and a lot of expats make investments in real estate. My husband and I both do freelance work part-time from home with U.S.-based clients.
Activities: Yes to all your interests!
Here are a couple of sites you might want to check out, if you haven't already found them (I know there's not a ton out there about Uruguay):
I got a good sense of what it might be like to live in Uruguay from this blog. Once we moved here, we actually became good friends with the American writers and their nearly-three-year-old daughter. They recently moved to Bariloche, Argentina, for a few months, but take a good look around their blog and drop them a note, if you'd like. Lots of informative posts about life in Montevideo with a little one. And their values and interests are very in line with the MotheringDotCommunity!
If you can sift through all the real estate investment stuff (not my interest, but possibly yours), you'll find some informative little articles written by expats.
And, of course, let me know if you have any other questions!