Chain misfiled can cause drift, but not so bad on a cross cut, you'd have to have the depth gauges or rakers out of balance to cause a real problem. Usually the problem is worn bar rails or too wide of gauge bar for the chain.
You don't notice it in a crosscut when the chain is sharp, more as it dulls, but it's almost impossible to rip. The chain will either dive into the cut, binding the mill, or climb out of the cut.
Keeping the bar true is more important than keeping the chain sharpened even.
I got a bar grinder, I turn the bar over half way through the day, and true it up on the grinder after a day of sawing. For years I'd true the bar up by draw filing with a flat file, but bars work harden as you use them, the new bars seem to harden kind of spotty, with hard spots and soft spots, and makes them more difficult to true up by hand, and files don't seem to cut as good as they used to.
You have to make sure the bar gauge matches the chain gauge. The first rip chain I bought wouldn't cut for crap. I found out they didn't make 58 gauge rip chain, so the company sent me 50 gauge instead, and didn't bother telling me.
Chain drive links wear, and bar rails wear, combination allows the chain to run sloppy. Again, crosscutting, not a big deal, but a problem ripping. You can get a rail closer, but I just tap the rails together with a ball peen hammer. Set the bar flat on some kind of anvil, we used to drive an axe in a stump and rest the bar on the flat of the axe, put a length of chain in the groove, and lightly tap the rails closed, hold the bar at a slight angle so both rails are closing. Again, lightly tap evenly down the rail and keep checking the clearance by moving the chain in the groove.
It's a good idea to true up the bar with a file or grinder after setting the gap.
Everything wears faster, and is more critical when ripping. The bars have a tendency to spend more time cutting in a concentrated area, and the middle of the length of the bar will actually dish out, leaving that area with less support for the chain.
Carl