Sheriff is a step down from Texas Ranger. He has to be older though because obviously Kill Bill was made several years after FDTD. He dies at the beginning of FDTD so naturally that means its after KB and Planet Terror.
Although Death Proof takes place in the present day, so if McGraw shows up in that, I dont know what it means.
Or maybe…just MAYBE…you take this Tarantino Universe timeframe bullshit a bit too sersiouly?
spits in a bucket and flips his hat