I don't know what I think so far. I'm not as thrilled as I thought I would be. It gets a TON of content. It has "memory units" that you configure on the MSN Direct site with your subscription according to what content you like (you can have 10 news sources out of 20-something for example). Overall, it's a ton of content but little things are bugging me like with news. When I read the news, it does a standard scroll of all the news stories but it doesn't let me organize them into categories at all, so I'm reading stories that I'd really rather skip over. It would be nice if it had categories. The weather section is nice. It gives you current temp, three day forecast, and international weather. The movies section is awesome because you can find a movie anywhere and everywhere. I'm half satisfied with the sports section. You program your "favorite" teams into it (you can have 5 per league) and it gives you game times and information only for those teams. The plus side however is that it gives you all the playoff information for that league or sport. The daily diversions channel is cool, fun stuff to read every day. I don't have horoscopes or lottery enabled due to lack of memory. Overall, I think it's probably worth it but I can't say how happy I am with it yet. I don't know if I have a moneyback guarantee during my first free month (do I?) or if I'm stuck. Either way, it's a ton of great content, some of it could be organized a little better though. I can tell you however that a lot of it is jumbled and the news headlines, and hi/low temperatures is more than enough if you're happy with it so far. The news section is REALLY big when you upgrade, but it means nothing if you can't easily navigate it. Same goes for the sports section and how it doesn't organize well. I think I'll end up keeping it because it would suck to lose functionality now that I'm used to it, but I don't know whether I'd recommend upgrading it or not.
I guess the final verdict is that if $40 isn't a big deal to you and you're using the watch a lot, there's no reason not to spring for the service. If it's tough for you to pay $40 a year and you're not using the watch a ton, pass on it.