The Long, Slow Climb
I make no secret about it that I run Slackware on both my server and my desktop workstation. Slackware allows me to manage my systems the way I want to, without a "nanny" holding my hand and saying "No.". And, with this level of freedom comes a corresponding level of risk; you can really fsck things up as Slackware doesn't supply a safety net. But, that's all right: I believe in learning skills, and Slackware certainly requires skills.
When it comes to software upgrades, Slackware stays true to it's philosophy. The Slackware upgrade process is simple and easy, and you can just as easily corrupt your system as upgrade it. It takes some skill to do it right.
Well, I've just (successfully) upgraded my desktop from a very back-level Slackware 13.37 to a slightly-less back-level Slackware 14.0. And, I plan another upgrade soon, leapfrogging to Slackware 14.2 on both systems.
The hard part, for me, was how I would manage the upgrade of software that I had built myself. These applications and libraries do not come with a Slackware package, and I have to "upgrade" them by hand, locating compatable releases of the source code, compiling them, and building Slackware packages that target the upgraded system. Up until now, I've depended on the "checkinstall" utility to build packages from source, but, this time, I decided to use the Slackware native "makepkg" tool.
Makepkg has its benefits; it's part of the official Slackware toolkit, it does it's job simply and without extra software, and it allows more freedom to build custom components. However, it takes a steeper learning curve than "checkinstall", and it comes with almost no documentation. "Checkinstall" also lacks documentation, and hasn't been maintained for years. So, I learned "makepkg".
It took about two weeks, from start to finish, but I've now got a running, stable, customized Slackware 14.0 system running on my desktop, and a new tool in my toolbelt. My next step will be to upgrade the desktop to Slackware 14.2, and use that learning experience as a guide for my server's upgrade.
It's going to be a long, slow climb to the current release of Slackware, but I can do it. I have the skills and I have the tools.