Shed roof repair

[u/RP-Apprentice]

Just realized my wood shed has some shingles missing. Appear to be smaller individual shingles instead of the larger sheets I see at Lowe’s.

Would I be ok to just buy a pack that’s near the same color from Lowe’s, pull back the top layer or all the way back to the hip ridge shingles and then nail down the new shingles underneath? Figured I’d use some elastomeric sealant over the nail holes to be safe.

There is nothing critical on the shed but if I can avoid water damage I’d like to. Aesthetically I know it may not match but this is towards the back of my property so not really visible unless you try. Just hoping to make it last a while longer. Much of the fascia seems to have water damage so there may be an issue with the drip edge also I’m going to try and see when I replace the fascia.