1.
If you have DR 3/-, DR 5/Cold Iron, & DR 10/Magic then...
*Getting hit with a +1 Longsword bypasses Magic, but not Cold Iron, -5 damage.
*Getting hit with a Masterwork Cold Iron Longsword bypasses Cold Iron, but not Magic, -10 damage.
*Getting hit with a +3 Metalline Longsword bypasses Magic (+enhancement bonus) and Cold Iron (property of metalline), but not the DR 3/-, -3 damage.
None of them stack, but the best applies. It's to say you have three separate Damage Reductions there, not one called DR 18/Magic or Cold Iron and -. Similarly, having Damage Reduction 3/- from your armor and 5/- from a Class Feature won't stack and only the best (5/-) applies.
However, do note there is some Class Feature/Feat based DRs that do note they stack. If they do, apply them separately. Like in the above, if that DR 3/- stacked, then a +1 Longsword deals eight less damage, -3 from the stacking DR and -5 for the Cold Iron.
2.
You are correct with your Operators.
*Cold Iron or Silver would mean either Silver or Cold Iron will bypass.
*Cold Iron and Bludgeoning would mean you need both a Cold Iron weapon and Bludgeoning damage to bypass.
3.
It's easier to list what Damage Reduction applies than than what it doesn't. Per Rules Compendium: "A creature that has damage reduction (DR) ignores some of the hit point damage from weapons, natural weapons, and unarmed attacks that don’t meet certain criteria." Which is semi-accurate in the details imho. DR doesn't apply against any Energy-like damage and untyped damage from spells. However, there is a few spells that deal Bludgeoning and Slashing damage, typically they note DR applies but mayhap not in every instance. A good rule of thumb for handling those is if the damage is type cast as Slashing, Piercing, or Bludgeoning, then DR should probably apply.
4.
Damage Reduction doesn't apply to Falling Damage unless you think the planet is making an attack roll using it's body as an improvised weapon. In which case I suggest you your self picking up Damage Reduction, because books may be flying in your direction. Same for Crushing damage if pinned under a house or dungeon. See the Rules Compendium entry: "A creature that has damage reduction (DR) ignores some of the hit point damage from weapons, natural weapons, and unarmed attacks that don’t meet certain criteria."
Did I cover everything?