I'm sorta in agreement that "any in to any out", and "any out to any in" would be cool. I used to build gargantuan patchbays for studios (my own included) that provided that level of flexibility - albeit not without drawbacks, it was complex to manage, and it was possible to create some truly awful routes!!
The only software I have ever used that provided that level of flexibility was Bars & Pipes Pro for the Amiga, but it was MIDI only.
These days I lean towards it ought to be possible, but not the default behavior. It is too easy to lose track of what goes where already! I had this discussion with Ron K a long time ago - the result was that the best way to do this would be to "Add new Bus Output", leaving the current Bus Output limited to one destination. And once you have to insert a second output widget there is no real benefit over using the existing "add send" command.
The automation issue - if I am using the Post Fader setting for the send then (I think) automation is already captured.
I also think the Post Fader setting captures all the FX bins, but not the FX sends, since those do not return to the channel strip, but that's precisely why one would use a send instead of the FX bin.
So I've stopped thinking about this as a work-around. But that is just me. And now that Keni brought up the automation question I guess I need to go do some experiments... but I've yet to run into a project where it caused problems... at least that I noticed!
HOWEVER, I do use SideChain Mixer from time to time to do things I wish were native to Sonar. As an example, I still like to route delay and reverb outputs to the sidechain input of a compressor or gate. It is a strange effect, and not one you can use on every project, but it can be cool. There are others, none of which come to mind right now (need more coffee!!)
Which makes my vote something along the lines of yeah, add the capability, but don't let me select two outputs from a track too easily. And let me route tracks to tracks, and tracks to side-chain inputs, and, and, and...