What would a hypothetical (or actual) $50 to iTunes every month get you? Quite a lot of great stuff, actually. Here are some suggestions…
1. TextExpander for Mac — $34.99
Pricey, perhaps, but if you have iTunes credit laying around you can use it to purchase TextExpander 3.4 from the App Store. Despite the fact that the big version 4 update that just came out is not allowed in the Mac App Store under sandboxing restrictions, you can buy the version from the Mac App Store, download version 4 from Smile's website, and, according to a representative, it should recognize the license from the App Store. There is an iOS version also available for $4.99.
2. Prometheus in HD — $14.99
The movie got pretty good reviews. If you're not going to buy it, and you haven't yet seen it, it is at least worth a rental.
Grand Total: 49.98