Rip once, to flac, ape, or wma lossless.
Connect your handheld device and then set the options for that device.
In options, you ensure that mp3 is set as a supported format, and set the encoding settings.
MC will convert from flac to mp3 during sync.
You also have the option to tell MC to keep a cache of those converted files for use the next time you sync, saving you the time taken in conversion on later sync jobs.
Following on from that, you can also instruct MC to keep the converted files in a "stack" with the original file. The 'stack' is basically a link between the two files, so, tag changes to the 'stack top' are propogated down to the stack, and if you delete the original, you also have the choice of deleting the lossy file too by way of a check box on the 'delete' dialogue.
The lossless file will be the 'stack top' which means that for general library use on your PC, it's all that you will ever see, MC will manage the lossy versions in the background for you. MC's handheld options really are of the "set and forget' variety. They work, and work well, leaving you to concentrate on what you want sync'd and nothing else.
Your digital player plays wma files?
It's not a Zune is it? Unfortunately, MC does not support the Zune.
-marko.