the answer here is not 100% known, but roughly you have to stay above 80% starts. 20/25 is 80% and i think that last check for pinging you on promises is just before the season ends, which lets people squeak by with 20/26. also you don't have to start after the regular season but apparently there is one last check to un-ping you on promises sometime during or after the CT. but anyway, stay above 80% all season and you should be fine.
during the season, if you say, skip starting him the first 6 games, his work ethic absolutely will drop. you will, however, be able to undo some of this damage, recovering the lost work ethic. but you lost work ethic growth and individual growth during the time his work ethic is lower. the guy won't quit, but it still hurts. the comment about not starting 2 games in a row always making them complain is definitely not true, ive done it a ton of times, early and late in the season.