> I guess I'm just spoiled, wanting a perfect migration ...
That would be one where you do not see the BSOD because you do not start the VM between stage1(imagging) and stage2(patching)
But that says nothing about the quality of the patching process.
personally I would use Coldclone to import a SBS
About your parallel port problem - if possible I would avoid everything that needs to be directly attached to an ESXi host - other than a USB-boot stick.
Using devices that server ports via network may be more expensive - but in the long run it makes things so much easier