Are the trails you will ride when the tour is over paved?
What do you know about the support on the tour? Does the support have an excellent reputation so that you know vehicles will be ranging up and down the road keeping an eye on you? Or is it more like they will be at the end of your 80 mile (or whatever) ride every day, and you'll only see them once/day? If the support is really good, then the risk is pretty low.
As for the compact double gearing, that really depends on what you know about yourself as a climber, what the mileages will be, and so forth.
I've found I can carry plenty of stuff for a supported tour by using the following combo: Jandd under seat bag, Bento Box, and rigging a small seat bag up front under my handle bars. I just use that one to carry my repair kit...that way I don't have to run into my repair stuff every time I want to grab some sunscreen or jacket out of my real seat bag.
If it was me, and you like the Ruby & it fits...for the riding you'll do after the tour, I would go for it. I might put a mountain cassette & derailleur on the back, just for the tour, to keep fatigue down day after day. But then, I'm overweight and a slow climber.



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