I know this is an old thread (before anyone mentions it) but I was dropping by looking for hints on gear compression (already did it on the Commander 114 but now I'm trying it on the Falcon 2000 series and it isn't behaving). I can answer the final three unanswered questions based on my own experience, if it is any use somewhere down the line.
I just make AI, so the animations I do are simple ones.
1/ I don't group the landing gear, the oleo is what I give the tag x_gear (where x is c, r or l depending on the gear leg) and I create it as a cylinder (3 or 4 sides at most since the a/c is an AI one) that I draw downwards, that way the pivot is already at the right part of the leg, the top part. I then *link* the gear components to the x_gear oleo (wheels, axle mechanism, compression struts and any other gubbins that rotates with the leg (eg a landing gear light too).
2/ That way, they rotate with the gear leg. Naming the tyres correctly means they move with the gear leg in the x_gear animation and also rotate by themselves on the ground - the c_tire etc labels - through their own pivot points. The x_gear names and the x_tire names enable their particular animations when they are needed, and could probably do them simultaneously! The sim recognises the name and does the necessary work.
3/ The tyres are *linked* to the gear assembly as already mentioned, to move/swing with it as it retracts, but if you use a correct component name you get the rotation when the vehicle/aircraft is rolling on the ground (and for a few moments after take-off). This is c_tire, l_tire_r_tire or one with a number suffix for gear with multiple tyres (eg c_tire and c_tire_01 for a 2-wheel axle). If the tyre rotates the wrong way, you have the rotation axis backwards, and you just need to change the component's pivot point (select object, click hierarchy tab, choose "affect pivot only", use the rotate tool to grab the vertical axis of the pivot and rotate it exactly 180 degrees (unless you like wobbly wheels). After that the wheels roll correctly.
As already mentioned, simply by using the x_tire (where x is again c/l/r depending on the gear assembly) nomenclature you'll get rotating wheels, you don't need to animate that for yourself.
After all that, you also link the c_gear to a stationary component in the aircraft (a flat plane will do) called c_wheelwell, the r_gear to r_wheelwell and the l_gear to, you guessed it, l_wheelwell. What the wheelwell name does is make the gear disappear entirely (stops it being rendered) when it is fully retracted. For AI and for UI aircraft this removes a lot of polygons from the rendering of the aircraft and makes it a smidgin more efficient on frames.
I've been modelling just for 2 months, so there may be other expert advice, but what I've described works for me.
So, I may not have answered your question, sfh294, but the next "me" that comes along might benefit from this, FWIW!