Is there a simple way of sidechaining a track to the kick within Maschine 2?

Not sure what you mean by "pulling MIDI/Audio out" but sidechaining is as simple as this:

To me this looks exactly the same as it does in Ableton:

The same goes for nearly every dedicated controller, it's built to control its own software as opposed to a generic MIDI controller. The same goes for Push-2 or MPCs to a varying degree of nuances when used to control other stuff. For generic control, you're better off buying an MPD or Atom like controller.

Oh, OK, no problem. In that case, I would assume you want an audio track for each Maschine Pad in Ableton so you can mix the drums from the DAW, you just set the output of each PAD to a different External Audio channel, then create an Ableton Audio track for each and set them as inputs:

Now since you have an Audio Track per Maschine Pad you can use the sidechain normally, exactly how it works by default in Ableton. The 1st external Audio output from Maschine is the track where the Plugin is loaded, that's why the name on the sidechain pic above is "2Maschine Plugin", that's where my Kick is.

As for the MIDI it depends on what you want, Maschine by default has each Pad in a different MIDI Channel, that's why it creates a bunch of Tracks when you drag and drop the MIDI, to fix it right-click the Group and select:

Group MIDI batch Setup> Sounds to MIDI Notes

Now if you drag and drop it will only use one track, where each note triggers a different Pad. Now head over to the Group Input Settings and change it to Manual and you're done, save the Group or Project as a template so you never have to do this again.

XLN XO is way simpler because it's only designed for drums, while maschine can also have instruments, groups, sequencing, etc... It's a far more complex SW, therefore it needs routing flexibility which complicates things for new users, this topic is where I see the most confusion... so you're not alone.