I’m a rather parsimonious fellow, and I make no exception for chess software. My investments so far have been modest: 20 bucks on Chessmaster 10th edition, money well-spent thanks to the lectures by Josh Waitzkin. Other than that, I’ve been using AquariumDemo (free) for making my gifs and annotating my games, and BabasChess (free, Crafty included) for computer eval and playing on FICS. AquariumDemo has also been my “database” software. I haven’t really gauged its database capacities yet, but I think it’s time to start working with databases in earnest, and to that end I’ve started looking into SCID. SCID offers all the functions I’ll likely ever need database-wise, is deliciously customizable, also optically (something that’s dear to my heart), includes the Toga engine (ELO 2600), and is absolutely free. What’s more, the excellent Katar has two excellent SCID workshop vids up at his new place, and I also found two large free pgn databases with a ton of ELO2000+ games, the Million Base 1.74 and the ICOfY Base. Plenty good stuff, for no cost whatsoever. If you have any other recommendations for free chess software, sharing is much appreciated!
Update: Following Tanc’s recommendation of the Chess Position Trainer, I came across this article on chess.com about how to practise your opening repertoire with SCID and CPT. Haven’t read it in detail, but certainly will later tonight.