The Chisos No. 5 is my 3rd pair of Chisos boots, along with two pairs of the No. 1s. I'm fortunate to have many boots in rotation ranging from beefy PNW boots from Nicks to exotics from Lucchese. But I always come back to my Chisos to slip on for day to day use.
Dressy enough for the office, comfortable enough to walk miles, and robust enough to stomp around the dance floor, I can't express how versatile my Chisos have been. I used to draw a hard line on no foam/rubber insoles for my boots (and I still believe that once broken in, nothing beats a leather insole perfectly molded to your feet), but I can't deny that the Chisos insoles make the boot incredibly comfortable out of the box. You also still get that molded leather feel after wearing them in since there's a thin leather layer on top of their rubber insole.
Build quality is also up there among all my boots, with thick leather, tight stitching, and solid construction. I'd recommend folks check out Rose Anvil's videos on YouTube showing a pair of Chisos cut in half. Compared to the cross section of other brands, the Chisos use real slabs of leather in their construction with minimal synthetic material, and you can really tell the difference in quality if you've spent time around real leather boots.
I will note that, similar to other reviews, I did get some of the red leather dye leach onto my socks, especially if I'm sweating in these boots. Good thing the vast majority of my socks are black so it's been a non-issue.
I love the Chisos packaging and attention to detail. The boots come with a pair of cotton drawstring boot bags, which I typically purchase separately to keep dust off my boots when they're off rotation so that's a great addition.
I also received a handwritten thank you card. The third card for my No. 5s referenced my previous boots, which is a small but nice detail that makes you feel like you're really supporting a small company instead of some massive corporate entity.
I could be wrong, but I don't believe Chisos offers a resole/recraft service. They should! I know there are many capable cobblers and excellent leather outsoles (JR oak tanned leather is king to me), but I like to send boots back to the original manufacturer for work when I can.
All in all, my Chisos have all been great and I look forward to getting many more years (and miles) out of em.