Welcome to the forum, @ameadow ! :)
re: grasses There is currently a profile of a prolific grasses identifier that has some tips for grass observations that might be helpful.
I often link observations over time using “similar observation set”, which you can read more about here, but know others use “same specimen over time” when they are 100% sure they are photographing the exact same plant (might be harder with grasses, unsure).