It is well-reviewed, but that brush looks awfully...busy to me...
Don't order from the CAC--it's where all the returns go and the SA can't look them over for you. I, like others on here, have had terrible luck with CAC seconds. In my modest opinion, you should buy shell firsts at $650 if you're willing to pay $527. But, it's not unusual for the shell seconds to go on sale for $399. And whenever a new store opens they have a 15% off sale and you can order shell firsts for $552.
I think that is a wise idea.
Try stretching leather that's been wet from the inside, intuitively focusing on the spot that your toe hits. You can't do any damage to the shoes with the stretchers that you have--they'll break before putting too much pressure on the shoe. If you had an all-metal stretcher, you could damage the shoe or stretch it to the point that it didn't match the other shoe. (Don't ask me how I know this...)
In my opinion you should be looking at this in terms of more than just color. Leather texture and styling are going to give the boots a very different vibe, even if they were the same color, which is not the case if you're considering the Higgins vs something in dark chili. Anything AE offers in dark chili is going to look more upscale than the Higgins, even paired with jeans. According to a SA I trust the Higgins color is is more like milk chocolate, different from dark chili which has more red in it. I happen to really like the chili, I consider it very rich and classy, and to my taste it goes better than oxblood with all but the darkest blue jeans. But in any case, you should see it in person and judge for yourself rather than trying to make in a priori determination based on discussion board comments. After all, you don't have to wear them to decide if you like the color, so you can always send them back :-)
My god, there's no way they should be sold as seconds. They should have FR stamped on the soles and be sold on eBay as thirds. That's assuming no structural issues, if that seam is integral to the shoe they should have just gone into the trash.
Something about that shoe bothered me, but I couldn't quite put my finger on what it was. It's built super-casual and for lack of a better term, "new-age" look, that doesn't fit with a traditional medallion, IMO. It's kind of like a mullet, business in the front, party in the back.