Textmate, Propane, LittleSnapper, Things, are all software I use for work that I own the licenses to.
I use google docs over MS Office.
Photoshop is the elephant in every room though. $1000 for creative suite. Lots of people in the development cycle use it but not as a primary tool. Buying it for every seat in your office is expensive as hell.
If it were my company and we were bootstrapping, I'd probably pirate photoshop, use google docs as much as possible, buy keynote, pirate windows for the QA boxes (damn you IE!).
I think there's a line crossed if the company wont buy any software. If there's no respect for software developers, there won't be respect for you.