Shaf, I already have my way to sync:
1.- I have a view with filters of the files I want to sync (instead of an smart list)
2.- I build cache for my lossless files, with a handheld, since the build cache on background feature doesnt have full encoder dialog (I dont want 320kbps or 128kbps, I want lame v2, please Jim help me out)
3.- I select my sync view, and select all files inside, and right clic > stacks> expand stacks
4.- File > Export to iphone & itunes
Itunes can only take lossy files, but as I have mp3's as cache of my lossless files, there is no problem.
5.- Once the export is finished, (all files remind selected) right clic> stacks > collapse stacks
Is the easiest way I found to sync to my device, and I have been asking for improvements on MC to make this more usable and easy, and JRiver IS responding, the cache on background is now added, I hope the other things will be implemented soon, as full encoder dialog on background cache and some "automatic" export of cache files to itunes (to not have to expand and collapse the stacked files)