Keep in mind that I'm a noob -- I don't own NSTs, for example, but hope to soon -- so I'd love to hear other opinions.
Also, I didn't consider bicycle toes because they are uncommon and also disgusting IMO.
This is the right approach to thinking about shoe trees. The wood in the shoe trees do not absorb that much moisture -- some higher-end shoe trees are even lacquered. Their main purpose is to keep the shoe's shape. And you want to do this while the leather is still warm from wearing.
In practice, you should be rotating your shoes in such a way that the moisture would have had plenty of time to evaporate anyway. So the effect of leaving the shoe to dry for some time before putting in the shoe trees is negligible.
Hey Ryan, welcome. I know it's like recommending Sgt. Pepper's to a music lover but I would go with the color 8 longwing. It's not black or brown, it's just this universal color that takes more effort to find a situation in which it won't work than one in which it will. You really can't make a poor decision though; you'll be happy with any Alden you get. Best of luck.