On modern Linux DEs, it would be similar to the Alt+F2 shortcut that pulls up the "run command" box. On KDE4, at least, you can do the very same thing by having documents and such show in the results as well. I actually like this change that Microsoft made as it really does improve starting an application or loading a document.

Odd. Maybe it's just the shape/size of the casing on the Captivate. I have the same little door but haven't had the issues you describe.

Comparisons:
Top of the Captivate
Top of the Vibrant

I have the Vibrant (the T-Mobile's variant of the Galaxy S) and have no problems with generic Micro-USB cables. Specifically, I have used the ones sold by Monoprice, and they have a huge block of plastic on them behind the plug instead of the thinness of the one that comes with the phone. Perhaps your cable is malformed in some way. Have you tried a different cable?

HTC uses a special Enhanced mini-USB port. It lets you connect headphones directly, for instance. I'm not sure why they include a special cable when a standard mini-USB would work just as well.

GarageBad? Does that happen to be the software StrongBad uses to compose music?