Any feedback is appreciated!
Looks like the toe medallion was stamped further towards the toe on the 2nds. If that's the only noticeable flaw (to the extent it's even is a flaw), I'd keep the 2nds. That said, at the end of the day it's up to you whether the difference in medallion placement is worth the $100 price difference.
Yes, you are buying defective shoes but hoping there are no defects.. contradictory expectations from everyone(including me)!
If you spend some time scrolling through the posts in the "What Are Your Wearing" thread in "Classic Menswear" you will see people all over the world wearing chukkas with suits or with ties and jackets. It's safe. None of them have been arrested by the Fashion Police.