I don't want socailism I want to be able to pay $5-$10 dollars a month to access all (most) music from any device without being locked into some moronic DRM scheme. It's not that hard.
That's too bad because in capitalism every person and company should be allowed to freely state their prices on services and products. What you want fits more into socialist system.
Can you tell me more about the amazing Microsoft SharePoint, which I can use in conjunction with fantastic business tools like Microsoft Great Plains to increase my productivity and my profitability?
No, but you can Bing for that!
If you're worried about your privacy from the party offering the service, you can't give Dropbox a pass.
Like you noted, you use TrueCrypt or similar. This is even a suggested solution by Dropbox team and it's a valid one, because you should never trust third party provider with your encryption.
However, at least Dropbox does more encryption on the data and actually stores it in encrypted form, even if they are able to obtain the keys. This is still vastly better than just using HTTPS or other "secure" connection between the client and server but still saving it unencrypted. On top of that HTTPS etc are subject to secure key forgery and man in the middle attacks like providing self-signed key and snooping the connection (a real problem in many less developed countries).
Single tasking: Just Say No.