Flutterby™! : A guide to systems for syadmins?

I've got a problem. I'm on the City of Petaluma Technology & Telecommunications Advisory Committee. One of the things that I'm interested in is promoting more open data. The folks in the city's IT department are strong believers too, every time I go poking through DataSF or PortlandMaps I get to thinking "heck, Petaluma has more of their data online".

One of the problems, however, is that a lot of the data is hosted in ways that aren't necessarily easy to mine. Petaluma buys a lot of drop-in software, some of it is hosted elsewhere. Often the problem with getting data out of the city is that the processes aren't computerized, or where they are they're not published in an easy to mine format.

I'm starting to write some Perl to convert what is available online to a form that I hope mine some of that data. I've written some bots to datamine Accela Citizen Access, draw building permits on a map. I've extracted voting records from Granicus hosted meeting minutes, so that I can look for voting patterns (oddly, I haven't gotten much excitement for that data set...). The latest hack, and one that might actually have some interest, takes meeting announcements and dumps them into Twitter.

Tim at the city is, rightfully, reluctant to take these hacks under his wing. He's got limited budget and limited staff and doesn't want to take on more responsibility without an economic justification or a clear directive from the town council. He's also worried about my projects pushing support load over on his department; the city's gotten phone calls requesting support and clarification and such that stemmed from a third party pothole tracking database. And they're a Microsoft shop, which means that they're not always able to be out there on the bleeding technology edge.

The upshot is: I'm happy to host and run these on my own machines. I want to make these processes as reliable as possible so that I'm an ally to Tim, Trae et al, rather than yet another yahoo spawning support calls for systems that aren't theirs. If I can build reliable systems, I can build trust and work towards getting some publicity on the city web page. However, I'm not a sysadmin. I'm a coder with a different sort of release process who sometimes dabbles in continuous deployment and sysadminnery as a hobby.

Any of you sysadmins out there have suggestions on some reading for building and running robust systems? How should I set up test procedures so that I catch when apt-get upgrade causes Moose to decide that name is now a reserved member name and some obscure Perl script that I never thought to check the return from because it's been working flawlessly and has no real failure mode decides to spew trash? What's the best practice for a process that deals with an email that may only be sent once a month, making the test cycle rather long? How do I best track all the cron jobs and interconnected email addresses and web spiders so that when I'm moving some system to another machine I get everything?

Does this book exist? Or is that list about the best run-down on where to start building such systems you know of?