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.