I knew i would stir the hornets nest with you on this one because Old School Canes will always be #1 in your book - and i respect that. It's just my opinion though on Stoutland.
Kehoe is a Miami legend. He's earned a ton of respect for what he's done here, who he's helped produce, who he's put in the league, etc. He was one of my favorite position coaches growing up (Soldinger being another). He was a great college coach for a period of time but i see Stoutland as being one of the better OL coaches across all leagues, college and pro, during his time. If you talk to NFL people, that's how he's viewed, the way Hudson Houck used to be talked about during his tenure. Stoutland succeeded at Michigan State with top rated units, succeeded at Miami, succeeded at Bama and then succeeded in the NFL. He even turned a Rugby players into an All-Pro. He has a history of success, development and progression at all stops and all stages.
Kehoe had some great years and developed some great players (your list above) and great units, particularly the 2001 line, but he also had more than a couple bad years where people were ready to run him out of town. He was fired a few different times and never succeeded elsewhere. You mentioned Winston above.....the line that included Winston, who was an AA tackle, was terrible pass blocking unit. Before Stoutland left, he recruited 3 NFL linemen in Linder, Feliciano and Henderson.....those guys mixed with Flowers never quite met expectation as a unit under Kehoe that i recall.
Also, i know most articles credit Kehoe for Searcy, but the OL coach those seasons was Gregg Smith, was it not? Kehoe was an asst OL coach during that time.