Why not send your bags with the folks who will for sure get there 1st, then all you have to do is haul arse to your connecting flight?
That's the plan - at least to the point where I don't put them at risk of baggage limits. I've emailed the Meet and Greet people as well - figure all I can do is set everything possible up to give me the best chance (carry on only, front of the plane, waitlist for the better flight, check in before leaving, etc.) and then hope for the best. Even if I get stranded, it's not like I'd be in Cleveland or something. (Apologies to Cleveland natives.)