I updated my 295 once - about three years ago. I got the disk of ebay - a real one, not a knock off which made it a little cheaper.
It's a great unit but I don't use it for the info (that's a PITA to get to anyway) I just use it for speed, heading etc and the maps to see if I'm busting Bravo airspace. If they ever change, then I'll update the database.
It's a backup really. If I was in IFR, I'd have it updated regularly. (ok, and it'd be a 430 anyway)