I used to do fresh installs (due to a general fear of incremental upgrades failing) until I tried using their upgrade guides. I've never looked back. http://www.openbsd.org/faq/upgrade54.html
I do upgrades on some machines, but for some servers (firewall, dns, print server), it just takes a lot less time to do a fresh install. I keep the configs, keys, etc. under source control and can put it all back faster than doing the upgrade.
It is also pretty good practice for anytime those servers go bad. It helps to be able to put temporary replacements in service from whatever I have lying around. I can save the hot spares for machines that have user data on them (e-mail, file servers).
I seem to recall someone (Theo, I believe) say that in order for an OpenBSD to maintain library compatibility with existing applications, you had to do an "Upgrade in Place" - and not do a fresh install.
I.E. The default approach, incremental upgrade, is the only way to ensure your OpenBSD system doesn't fail.
For the servers I'm talking about, blowing the whole thing away and installing any packages from the new disc is just fine and keeps away the clutter.
I look at it this way, if all I'm really doing is adding some flags or configuration files, I would rather just blow it away and do the reinstall. Last couple of times I did that with my firewall, it was a 20 minute install.
Completely agree with you - and it's what I've done in almost every case. The Library thing is an OpenBSD issue that people who are upgrading need to take note of though.
Groove Salad is very good, but sometimes it reminds me of porno music. I've been rotating between Space Station Soma and the Dubstep channel (which actually plays quality Dubstep (if such a thing exists)).
Soma.fm is one of the websites I like giving money too, I only wish they had cooler things in their store (I've got the mug, and the hoodies/t-shirts aren't too appealing to me).
To counter all the neutral to negative feedback, I want to chime in and say I was very impressed. The execution speed with the aesthetics excite me. The gazillon-terminal-window- opens junkie in me always looking for a better terminal emulator -- especially with reasonable Unicode support. Keep up it the great work EFL team!