Listen to the people here - they are wise beyond their years (and some of them are as old as dirt!!!).
Like them, I've been doing this a long time. That doesn't make me an expert, but I can state unequivocally that if you set out on the trip that you described on your first post, you will have a miserable time and will regret the day you thought of the idea. You will, trust me. The absolute BEST possible scenario I can think of will be that on about day 5 or 6, you will muster up enough courage to tell the others that you love them, you still want to be friends with them, but you simply CANNOT continue on this trip with them, and you are hereby setting out on your own to salvage what is left of your bucket list adventure. Hopefully when you get back, you still have a wife.
How's that for scaring you?
There are just too many personalities. Too many riding styles. Too many expectations. Just too many. And because you are the "organizer", they will blame you for everything. Your organizational skills will drive you to salvage things. You will try to find compromises and you will fail miserably and in the process, make yourself miserable.
If all of you had 50,000 miles of riding together under your belt, it would be totally different. But it's not.
Here is some other advice I can offer:
The more I do this, the less I plan. My Spring 2016 tour, about 10 days and 2700 miles worth, was COMPLETELY unplanned. The only thing my buddy and I knew was the general direction we were heading. I spend my whole life in a box. My every day is planned to the umpteenth hilt. It's exhausting. When I tour on the bike, there are no plans. The unkowning is absolutely exhilarating. In today's world of cell phones, GPS, etc, let's face it, you can't get lost and you certainly have to work hard to find a paved road with no help available. Also, planning to see "this, that, and the other" is a good general idea. But by all means, leave PLENTY of time to just wander. Get to that road crossing, look left, imagine what's around that next curve, and then just do it. Every brain cell you don't use for planning, sticking to the plan, and worrying about the plan is a cell that you can now direct to enjoying the adventure. Look - don't be stupid about it. Have a general idea of which direction you are going. But after that, take a small risk. You will NOT be disappointed. With out a doubt, some of the best stuff I've seen on motorcycle tours - some of my fondest memories, were of things that just appeared on the road out of no where. I had no idea it was there, but I had time and took a chance.
Now - you can't do this ^^^^ with 5 people you haven't ridden with for 2 weeks. You just can't. You could try a simple itinerary - shoot for "_____ place" in a couple of days. Then break off in groups and agree to meet there then. Next meeting is in 3 days at "_____ place". See ya'll then. I've done that and it works pretty good.
As for your highlights you wish to see, I've been to many of them and I can tell you that I could never see all of that in 2 weeks. It's just too ambitious for me. If I'm trying to get somewhere, I can ride 800 miles on the slab in a day and I've done it a few times. I don't want to, though. I'd rather ride 250-300 miles on the back roads and see some stuff. Your list is either 4 weeks, or more likely - 2 or 3 separate trips.
For example - you can (and should) spend a week alone in the western Colorado/northern Arizona/Utah region. Zion, Bryce, Canyonland, Needles Overlook, Cedar Breaks, Monument Valley, 4 corners, Grand Staircase, Natural Bridges, Arches, Million Dollar Highway, north rim of the grand canyon, Durango, etc etc etc - that alone is a week at MINIMUM. If you like to hike - just as a small example, you simply have got to walk up to Angels Landing in Zion. It's a spiritual experience that few people ever know. But that will take you no less than a 1/2 day by itself. It's worth the time - mind you, but time it must take.
Respectfully and with all the friendship I can describe - I think you should re-think this whole thing on a grand level. I'd love to and be happy to share much more with you, but before going down that rabbit hole, I'll refrain to get a better idea of what you are thinking.
.
