The cut in chain guard is "normal wear".
What you really need to pay attention to is the chain slider. The protective piece on the other end of the swingarm near the countershaft sprocket.
It's a normal wear piece too, but if the chain eats through that it'll start cutting into swingarm. Not a good thing.
There threads around here on that too.
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2008 WR250X
Gearing: 13t - 48t
Power Commander 5 / PC-V
Airbox Door Removed - Flapper glued - AIS removed
FmF Q4
Bridgestone Battlax BT-003rs