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I recently installed Debian Wheezy onto a hard drive I later intend to connect to a different computer, though the computers use different brands of hardware. Will this work? Or am I setting myself up for failure?

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It will work as long as your initial system is not 64bit and the target 32 bit. If you set things up on a 32 bit system and your target is 64 bit you will have some performance hit.

Make sure you don't install proprietary hardware changes (like NVidia kernel patches) if the systems differ there (but Debian might not have those in the first place).

I have done this with SuSE and Ubuntu, first installing in a VM, then copying things over to a real system.

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Excellent! Thanks. Both of my machines are 64-bit, so it shouldn't be a problem. –  Shaun Gillies Jan 18 at 7:56
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If the graphics chips on the two machines are different, the installer may only have included Xorg drivers for the first one. So if the GUI on the second machine fails to start, that's what happened. This is not a big deal since you can then easily install the second set, and sans an explicit config, I think X now figures things out when it loads. Note the Xorg drivers are not the same as the more important kernel drivers -- those should all be in place since they are usually all installed as part of the distro kernel. –  TAFKA 'goldilocks' Jan 18 at 10:07
    
The other graphics related issue would be if you install ATI or Nvidia proprietary drivers which include a replacement openGL library. That library won't work on a machine without the same card (or at least, the same brand card). –  TAFKA 'goldilocks' Jan 18 at 10:10
    
What @goldilocks said. You will also have problems if your target machine has very different hardware you may be missing drivers that would normally have been installed and will need to manually configure hardware that would have been detected automatically by the install process. –  terdon Jan 18 at 14:12
    
@terdon : I think most distros just install all the modules the kernel was built with, which for distro kernels is pretty much everything, because they must be usable on a wide range of equipment. E.g., if I look in /lib/modules/some.distro.kernel there's way more drivers than any one system could ever need + the kitchen sink. However, I don't know if installers build a custom initramfs...if they do, that may be a problem, since it will include drivers for accessing the disk with the root filesystem. In which case you'll need to create your own containing the drivers for both systems. –  TAFKA 'goldilocks' Jan 18 at 14:31
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