Some things I've learned in this migration process, and over the years of hosting all my own web services, like FTP, email, DNS, and webserver:
Jerkwads abound: Spammers, and hackers. The amount of spam my domains received was getting insane. In fact, I'll be retiring my old domain just because I'm sick of managing all the spam, and wasting bandwidth. Even though its no longer 'my' bandwidth, it still annoys me. Running a blog meant that every post had 25 comments from bots trying to sell ED medications.
Trying to keep up with the spammers is a full time job. When the Bayesian spam filter "Spam Halter" became available, I plugged that in and trained it for a week or so, which dramatically reduced spam that hit my inbox. Still, some still gets through. (plus the server still downloads the whole message)
On the hacking front, I could look at my logs and see brute-force password attacks on my FTP server practically daily. I'm not even sure of other ports that may have been under attack.
Pick a version and stick to it: On a regular desktop, I always update to the latest, and usually don't get burned. However, with 'server' software this isn't always the case. Server software moves at 'internet speed', which means there are new versions constantly coming out, and "Technology of the Week", or "Yet another scripting language" is rampant. An example being and upgrade to a new web-email client means a new version of PHP, which requires an upgrade to some other component, and so on. I think this is why older versions are maintained so long.
Pick an OS version, an apache version, a tomcat version, etc. set those up, and leave it.
I still run email and web, but DNS, FTP are gone. I use apache 2.0.x, Tomcat 6, and MySQL 5.1.
The Email server will get less use as I move a few domains off my server, but I'll probably won't retire it completely for a while. The webserver gets some use, and it's fun to have a little servlet sandbox.
So yeah, about tomcat. Now that I finally grok it. I like it. They also stablized things to there wasn't a million different connectors. It's now just mod_jk, and it's simple to use.
However, I did use (and like) C# and asp.net for a while, running a windows box, I have 'native' access to the CLR (I have no idea how well mono on linux is supported, but I can't imagine it's easy to use), and SQL-express lets me set up simple databases. However, when my old 1U server died, and I moved it, nothing worked.. then SQL-Express no longer worked ("service failed to start"). I simply gave up at that point. I used the MS solution at work, and it runs like a champ, and the tools are decent but there's also a IT department in the background.
For my own stuff, I've gone back to java, and found that it's actually quite nice nowadays. TOAD let me set up my database 'playgrounds' in a snap, and once I cut through all the nonsense in the tomcat docs, found out it's really easy to deploy a servlet. The last piece being that there is a decent java IDE now, Netbeans 6.8. Last time I used java was perhaps 10 years ago, and the IDE landscape at that time was a wasteland, so I'm happy to report that it's improved.
My friend Trimbo thinks I'm insane for running my own server ,and is a big fan of ruby on rails. He has a different use case, and I'm sorta set in my ways. I like java, and banging out a servlet with netbeans is pretty easy, and I'll end up with a JIT'ed app, while I doubt RoR has a JITer.
This post has gone on long enough, so I'll end it here. But now that the blog is back, I hope to start posting more often, and with more interesting topics. Hopefully I can figure out a way to import my more interesting posts from my old blog... I think they were stored as plaintext somewhere on my hard drive...
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