Transportation cost is not an issue since the difference is very small. I'm mainly looking at convenience.

But after reading your suggestions, I think DCA is probably my best bet. You're correct about the late check out, by the time I get into the airport it's really only an hour or two to burn. Find a nice restaurant and work from there would be an option.

Upgrades is important to me but for this trip I'll be booking in V, R class as an MVP, I've already thrown all my hope of any upgrades out the Windows on this one.