For $350 you could get a much nicer scope - check
http://www.tequipment.net/, I've been eyeing their digital scopes they had some specials on recently Im just broke for a bit from xmas and car insurance. In reality too...I've BARELY ever used a scope, although it does come in handy.
And yeah if you're near the Dayton meet you could prob score something nice there.
Logic analyzers - I used mine a few times but found it takes a while to set up, although it did help me find and fix a problem I would not have otherwise found. I got mine for relatively cheap on Ebay, just MAKE SURE whatever you get includes Pods (breakout cables) and CLIPS (usually these are worth or go for more than the unit itself).
To answer the original question, I really like having the Fluke, I think its indispensable to troubleshoot things that most people seem to ignore, and baseline a board, but they are something that should be considered an investment. I also had one issue where I found leaning on the Fluke bypassed or over-shot the actual problem at hand, so once a problem is baselined, the Fluke should soemtimes be taken back out of the mix.
Roadrunner had a great deal on one but he sold most if not all of it. You can try flippers.com for the pods or ebay.
Also I would definitely lean towards one with the serial option...while you may not use it every time, its pretty good for scripting tests.