How to do legal technology in your firm?

I'm on a couple email lists from Technolawyer.com which had an interesting post lately about how to "do" technology in one's law firm. The lawyer writing on the issue was balancing using an outside consultant versus doing it himself. This particular guy came down on the side of doing it himself saying it saved time and just saying it was too important to be relient on someone outside to get this sort of thing done. Is he right?

For the fairly minimal tech support I've needed since I went solo I've used an outside consultant...haven't really had the emergency breakdown where the systems crashed just as we needed to get some pleadings or something out the door. It's hard for me to think that a lawyer doing their own tech support is the most cost-efficient way to do things. Perhaps in your earliest stages where you don't have any employees, yes, but once you start to have administrative staff don't these people need to take over these functions? And then for the bigger projects use the outside "consultant"? What's the experience out there?

Bigger question that I'm personally dealing with right now, what tasks should be delegated to support staff and in what priority order? My current set-up is I have a law clerk who essentially does some court filing and legal research. Additionally, there's clerical support as part of our office suite that I'll use when big clerical projects need more support. I'm in the process of interviewing for another slot. What should this persons role be? In my mind, issue one is accounting/bookeeping. Our bookeeping isn't what it should be and doing billing and billing follow-up each month sure takes a lot of time. Second, I want to get some of the repetive legal tasks off my plate...basic estate planning, real estate closings. Third, just general phone/email follow-up when I get swamped with court/meetings.

Are my thoughts in line with your experience? I suppose how and when to delegate is somewhat related to practice area(s).