Just as you listed them...
1. J Gilbert tan wingtip boot on commando sole (Barrie)
2. Alden Madison chromexcel punch captoe boot on commando sole (Barrie)
3. Indy 403 (flat waxed laces)
4. Context Roy
I'd get whichever one is available on your size. Both are great. I have the J Crew PCT boot and love it. I have no experience with the tanker so I can't really comment other than they look great in these posted pics.
I really like my Leffot tanker boots. The style was not something that appealed to me at first, but it eventually grew on me. You can't go wrong with the Jcrew captoe boot, though. It's incredibly versatile. My advice, however, is first get whatever style appeals to you more.
I'm thinking the same thing about insoles, and they're on their way to Dallas! Kathi did mention that they have a couple more eyelets than usual, so that should help with the fit. I'm anxious to check out the color on them, hoping they're more red than "light cigar". Take care, Doc.
I'm on the east coast so tracking says mine won't arrive until next Thursday.
Yeah, that's my fear. I'd be fine if the Ravellos had a mini-lug sole or a danite sole that Alden doesn't do. I'll see how I feel once I see them in person next week.
The other thing I noticed about shell was that it fits a bit roomier than standard leather. At least this was true with the #8 chukkas and the calfskin chukkas I tried on at Alden DC a few weeks ago. Is this true for shell shoes in general or was this just a one off thing?