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I vote May 27th because of when the season will end.
I pulled out the calendar and counted ahead 32 weeks.
A May 20th start means that the regular season will end on December 28th and a May 27th start means the regular season will end on January 4th.
Normally the playoffs start on Sunday following the end of week 32. That would be January 2nd for a May 20th start, or January 9th for a May 27th start.
If I were a playoff team I would probably prefer to start the playoffs on January 9th instead of January 2nd.
Hence I will vote for May 27th start.