I have a theory about what is going on here, which for me, I've verified with my own experience. Theory: whenever the flow of data is interrupted, for whatever reason, the software cannot compensate, and loses the connection completely.
I had posted a few weeks ago that I was having a lot of problems losing the data connection when my home ISP was acting up. So, the wifi would drop out, and I would also lose all data connection on the phone even through 3G, even when the wifi was re-established. At the same time, I had programmed in my work wifi, which is very spotty. At work, my phone would search for the wifi, not find it, and again lose the data connection through 3G. Since then, my home internet connection has resolved (wifi works smoothly), and I deleted the wifi set up at work. No more lost data problems.
Until....last week. I lost the ISP connection at home. I rebooted, wifi restored, but the phone would not connect to data, and I needed to reboot. And then, the email server at work crashed. As expected, I couldn't get my work email, but I also lost all data connection for my comcast and gmail accounts, too. Any bump in the data road, and the connection is lost.
So, for me, as long as everything is stable, I'm fine. Much of this instability is probably not immediately noticeable -- how often is a wifi connection wonky, or even possibly the 3G connection? I'd be interested if others tested my hypothesis: strip down to what you know is stable, and see if that helps.