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D first and I third covers 44 words, and they fall into three families that barely overlap.
R takes the box between them about thirty two percent of the time, with A and E level at twenty and O at eleven.
DAILY, DAIRY and DAISY share their first three letters and split only across the last two, so landing any one of them leaves very little work.
DOING and DYING both finish with ING, which is a shape worth testing early because nothing else in the group ends that way.
DRIVE is the guess to open with, since it covers the largest family and its V is a letter neither of the other two families uses.
No. DIARY puts I in the second box and A in the third. DAIRY uses the same five letters in a different order and is the one that qualifies.
DRILL doubles the L across the fourth and fifth boxes. It is one of the few here that repeats anything, so most of the group reads as five distinct letters.
Because its words are the familiar ones. DRIVE and DRINK come to mind faster than the rarer entries on the A and E branches.