Your system will probably accumulate small breakage here and there over time, dependency hell, etc. I'd recommend to schedule a few hours for a proper install of Debian, to me it sounds like a much more pleasant approach. Source: hanging out in the Debian IRC channel and seeing desperate people who tried to switch repos.

As others have commented, breakage is to be expected.

I'm sure someone will share an unofficial crunchbang setup script (based on a minimal debian install) once Jessie becomes stable. Happened in the past already, works very well.

Crunchbang rocks, using it since 2009 on all my machines. Don't feel like moving to something else.

I tried updating a #! (Wheezy) system to Debian Jessie a while back. Massive breakage.

Yeah, I've done it, and it is harsh. Easier to do a clean Jesse install and manually set things up. Basically you would want the dotfiles from /etc/skel on a crunchbang install, and then several of the custom scripts (I think from /usr/bin) like conky-wonky, cb-printers, etc. A bunch start with cb-.

I've just rebuilt my #! laptop last week. I can't remember what I did to break it now, but I did. Anyway, I installed vanilla #! Waldorf, updated sources to Jessie, commented out Waldorf sources and dist-upgraded.

No really major dramas. Run cb-printers before the upgrade to Jessie. Icons do screw up a bit, but easily fixed by installing some similar Gnome 3 icon themes. I'm using cb-waldorf-xoraxiom and "Grey-Icons" at the moment. Everything else seems to work fine.

I really like the #! Openbox experience and have yet to find anything quite like it. I did try Archbang during this re-build process, but wasn't convinced on first viewing. I know I could just install Debian and Openbox myself, but then have to spend a lot of extra time setting up menus, conky etc.

I'll miss #!, as I've really enjoyed it over the last three years. I've no reason to install anything else right now, but in six months I suppose I'll go elsewhere.

I dist-upgraded to Jessie from my working Waldorf system (using now). It was a little faffy, but not too bad.

One problem I've got is black internal borders on some of my menus (e.g. network-manager panel menu), but it doesn't affect me much and I really can't be bothered to read the docs to sort it out. Any ideas?

This was the good thing about Crunchbang: a lightweight debian install that looked good and needed hardly any configuration to work well.

Heh, yeah I've done this since.

I installed base Jessie from netinstall image with no desktop, then manually installed slim and openbox, and started from there.

It's much cleaner this way