I think that the Gen V games are far better than the Gen VI games. I would consider buying Black 2 or White 2 instead of Black and White though if you're going to get a Gen V game. While BW2 do contain story elements from the first game, and having the first games allow you to use the IR feature to unlock a few more features for BW2, this isn't too big of a loss over what you gain from getting BW2. Primarily, there is a much larger postgame in BW2, including the amazing Pokemon World Tournament. So you're getting more content if you buy BW2, even if you're missing out on some stuff.
As for whether the games are worth $60, I would say yes. You'll certainly get your money's worth out of them if you like Pokemon. I've played through them multiple times, and just finished a run-through of Black version. They won't get any cheaper, and will in all likelihood just end up being more expensive as time goes on. That tends to be the trend for many popular Nintendo titles, especially the Pokemon games (you can look at the prices for all Pokemon games prior to XY and see). The biggest problem is going to be a lack of online multiplayer, since the servers have been shut down. But if you enjoy the single player experience enough, I would definitely grab em.
Also worth keeping in mind is that the new Pokemon games, Sun and Moon, come out on November 18. So that might be something you would want to get for Christmas instead.