There was a little interruption here in Bronco Country as we all celebrated Superbowl Sunday. Today the team flew back on a B764 with an Orange "United" decal over the usual blue United Title. I guess that matches the City Slogan of "United in Orange" [I know, bad joke]
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As to Q 19: I did fly an Allegheny DC-9 ORD to IND to DAY to CLE. I might guess the flight continued on to PIT. Dinner would then have been served PIT to NYC.
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As to the 5 airlines flying DTW to CLE, my only guess would be a Delta DC8 originating in DTW and filling passengers on the way to Florida [probably seasonally]. TWA didn't fly jets into CLE while I was there; Lake Central had DC-3s then some Convairs; Capital Airlines leased B720's from UA and flew to PIT then MIA [my first jet ride], AA flew 727-100s to NYC then 720s BOS-CLE-LAX, Mohawk and BAC 1-11s but had to fly through Elmira to go East.