Back at the Reinstall Mines
You install and reinstall enough of the same applications over and over again and you're sure to have some peeves. As I rebuild my main work machine today, these peeves once again naturally rise to surface consciousness. The application I hate reinstalling most? Anything by Adobe, particularly Photoshop or Illustrator. I've owned copies of both applications since they were 3.0.4 and 4.rubbish, respectively, and have bought the version upgrades all the way through 10/7. This results in a multistage installation process that involves installing multiple older versions (some of which can be safely removed later and some of which cannot), swapping CDs like they were swinging 70s wives, dusting off large 3.5" floppy installation sets and entering, in the case of Photoshop, 3 different product keys.
It's not that any individual upgrade path is all that ridiculous, but the sum of the parts and changing approaches to prior-version validation over time sucks. Suffice it to say, hypothetically, installing from media which I don't legally have a right to, like say the full media for version 6 and then applying my legal upgrade CD and key to version 7 would shave about 30 to 40 minutes off the overall installation process. Illegal? Probably. Illogical? Not really. Unethical? Hmm.
Illustrator 10 is worse, basically I have to leave version 7 installed or it breaks the subsequent 10 upgrade.
I should balance things out by saying there are applications out there that are sheer installation bliss, in fact they seem to be in the majority for my basic tools. Thirteen down, sixteen more to go.