You can ground everything together, as long as they're being run through the same encoder. You wouldn't want to ground a button from an IPac to the ground lead on an Opti-Wiz, though- each encoder needs it's own ground.
No, you don't have to run a line back to ground when you reach the end of the chain. One wire is all it takes.
Even though you can ground everyting together, you may find it's easier not to, though. Say you're doing a 2-player panel.. You may prefer to ground everything on the right hand side together, and run a line back to your IPac's ground, and then do the same for everything on the left hand side. This would result in two lines going to the Ipac, which is OK.
You also don't have to make a straight chain, from one to the next each time. You can do more of a star if you want, where several lines all go back to the same point. Basically, any arrangement that gives a path back to the grond terminal is good.