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Where Audacity quickly hits the wall in functionality for me is in a project where I need to do simultaneous edits on more than two tracks. <snip>
I wonder if "grouping clips" is what you're wanting to do in Audacity? Couldn't be easier to deal w/several tracks at once.
Open Audacity Help and search for 'Grouping Clips'.
Never tried that - I'll have to check it out. An example of what I'm talking about though is selecting multiple tracks, splitting them all at the playhead, and then drawing a fade in/out simultaneously on all tracks, or in some cases dragging the ends of one group of items from separate tracks onto the beginnings of others for a crossfade. This is extremely easy to do in Reaper, and I imagine it is also in Audition.