?

While it is always preferable not to check, the early part of your post makes me question what is going on here. A "2.5 week trip coming up with a lot of short connections and varying wardrobe needs between two weddings, a business presentation and multiple climates" might justify (if one ever needs to justify) checking a bag.

What are the "number of reasons" beyond the usual (don't want to wait for bags, don't want to lose bags, don't want to pay a bag fee) that you feel make checking a bag inappropriate here?