flickr, mefi, FogBugz, used to pay for O'Reilly's Safari. Bought the Instapaper iPhone client, if that counts. Made donations to a ton of services and people, mainly open source projects, web comics and such. Also donated to wikipedia, wikileaks, eff and a few others. That's all that comes to mind right now.
Hopefully, Songbird will take the Firefox approach and start innovating more. It's good to see it copy iTunes, because iTunes has a great user interface, but at some point, they'll hopefully exceed iTunes, just like Firefox exceeded IE.
I currently use Foobar to play my music library; the last.fm client to play custome radio streams from my friends, or based on my past listening habits, etc - and Songbird for mp3 blogs (I love the way it lists all mp3's on a page on the standard music library format, with easy download links), and to check the Songkick plugin. If songbird was lighter and snappier, it could take on all of the above functions for me. Hopefully as it nears 1.0, a lot of work'll go into optimisation and streamlining
Frankly, I think the idea is fundamentally broken. Having a "usability expert" click through a site won't give much more insight than reading a bunch of Nielsen's top 10 usability mistakes and then looking for them in your site.
If you want a truly usable site, you actually have to do real usability tests with a bunch of real users.
Obvious solution: Buy iPhone. Get approved by Apple as a developer. Write awesome application. Make 1000+ bucks a day. Buy every other cell phone on your list and compare them yourself. :-)
It's always the same. Apple introduces new Mac, it's priced competitively. Apple waits a year until it releases a new version and doesn't cut price while other manufacturers release new versions, so the Mac becomes comparatively more expensive as time goes by. Then, Apple releases a new Mac, and the cycle starts anew. Repeat annually. There's really no need to write these "Apple is cheaper" "Apple is more expensive" articles twice each year.
"If there's one thing I am truly proud of, it's that I've wasted all my talents, contributed nothing to the human race, and will not be remembered by generations yet to come."
If you're doing things because you want to be remembered for them, you're doing things for all the wrong reasons and will never be remembered for anything.
His main (and only) issue with the iPhone seems to be battery life. Interestingly, tests have shown that the iPhone's battery life is about on par (somewhat better, in fact, see links at the end) than other 3G phones' battery lives. However, people are using the iPhone way more than other phones, so the limited battery life is more noticeable.
So he basically returned the iPhone because he liked it so much that he used it way more than any other phone he's owned.
Simple solution: Turn off 3G when you don't need it.
The other issue present on the iPhone and not on most other smartphones is the lack of a removable battery. I suspect battery packs and power-related accessories are going to be pretty popular with the 3G iPhone.
I'm not sure whether saving money for a startup is a good idea. It might just be a copout, a reason why you can't yet start your own company. But you can. You don't need that much money to incorporate, and you don't need to quit your day job - you may be able to move to a cheaper flat, keep working something like 50% at your day job, and spend the rest of your time on your startup while still making enough money for a reasonably decent living.
We don't know what your issue is, so we can't give you useful advice that applies to your situation. For me, I'm finding that I don't want to work 100% anymore, and I won't work overtime anymore, and I don't want to live in a city anymore. I can afford to stop doing all of these things, so I will, and I'll do it before I burn out.
I've worked years for other people, and in those years, I have created nearly nothing that I own. Like you, I've had ideas, and technically I would even have had some time to work on them, but after a day of sitting in front of a PC, more sitting in front of a PC at home just didn't seem very pleasant.
I want to have more time and energy to work on stuff I actually own. And that's what I'll do.
But perhaps that's not what you want. We don't know what you want and why what you're currently doing isn't working for you. I guess the first step should be for you to find out what you actually want.