1. I think I've finally fixed the pesky middle-of-the-night uptime problems by installing Windows Server Monitor. It tests out a coldfusion web page every five minutes, and if it hits a failure in two tries, it'll restart ColdFusion services. I've had it running for the past few hours and it's already dutifully emailed me once to warn that page loads had gotten slow once (but didn't need to restart any services). I have a feeling this simple app will solve the uptime problems like we saw last night.
2. I didn't quite finish the database updates last night and will try to complete it today. It may be during daytime hours, but will likely only result in about 20 min of downtime.