Somehow I didn't see Lisbon nor Evora in Portugal being mentioned before. Both cities are definitely worth a visit, especially the latter, because it is in a region specializing in producing some fine wines and there is also good food in abundance. I recommend eating those typical cheeses and fish.
Speaking of cheese, in Switzerland places like Zurich and Montreux are also worth a visit.
My recommendation is the messenger bag from Vanguard called The Heralder. I use the largest variant with my 1D-X plus 3 lenses and a laptop or better an iPad. It does not scream "camera bag" and you can bring it as a laptop bag to strict business meetings without anyone raising an eyebrow. Apart from that I agree with Paul Walnut that the camera bag from Jack Wolfskin merits a recommendation, but this is a backpack, not a messenger bag.
I don't think IS is such a huge issue at 200mm, provided you shoot only in situations with sufficient light to use a fast enough shutter speed.
As long as you don't shoot sports you will probably shoot a 70-200mm lens at 200mm most of the time, because you will take that lens only in case you really need the long focal length. In this case purchasing a 200mm prime may be a good idea for you.
Yes. I've cropped the photo a bit. The picture was taken with a 100mm f2.8 L Macro IS lens and a 5D Mark III.
Regarding a comparison between a crop camera such as a 7D and a 5D Mark III used for macro shots it is important to note that even cropping I get better results with the full-frame body compared to the crop sensor body. The extra reach the crop sensor provides does not in any way make up for the pixel-level quality difference full-frame sensors provide. This also applies to the 1D-X.
Size difference is actually kind of a non-issue. Gripped a 5D Mark III or 7D is similar in size to a 1D-X. Instead there is a significant advantage for 1-series bodies in terms of better usability. Getting used to this is similar to the addiction to L-lenses. Once you have experienced just how good it can be, you don't want to go back.
Both investment in bodies and investment in lenses has resulted in my photographic output to become significantly better.
For me the effect has usually been a multiple of equipment cost. This is because I am always looking for highly specialized equipment that allows me to achieve a certain look or making a shot possible, which I could not hope to achieve without the prerequisite gear.
Exchanging a 5D Mark II for a 7D and adding investment in extra EF-S lenses does not appear to make sense to me. I rather recommend sticking to the 5D Mark II or perhaps upgrading it later to second 5D Mark III. This avoids unnessary complications with your lens kit.
Then again if you already have a good set of wide lenses you may also use a 14mm or 16-35/17-40mm zooms with a 7D. That might make the 7D a worthwhile investment, provided you use lighting equipment more than you would rely on available light.
Well I believe you already have made the best choice going for the 35 and 85mm L lenses. If you must stay within your budget you could also choose to concentrate your investment in excellent portrait glass, going for the 85 and 135mm lenses, although I believe the latter will become useful for you only once you add a full-frame body. I agree that on crop the 100mm lens makes more sense in this area.
During my recent summer vacation I have been shooting lots of macro photos. At first I thought I might use my 7D, because of the extra reach it provides, but I ended up using my 5D Mark III almost exclusively. Even with a 2x extender I got better results with the 5D Mark III than with my 7D. The 5D's sensor provides just so much more clarity and shooting macro at least I am always hunting for that extra bit of depth of field a smaller aperture will provide.
I particularly like the field of view offered for example by the 14mm L on a 7D. I would love to have a specialized L prime for full-frame with a very similar field of view. Of course it should deliver image quality at least comparable to the existing Zeiss prime.
I also shoot with both. In case of macro shots the 1D-X ability to more quickly acquire focus does make a welcome difference to the 5D Mark III. Although I tend to shoot with manual focus quite a lot using macro lenses (I use both the 100mm and 180mm L macros) I noticed a tendency of me using autofocus much more often with the 1D-X.
One application for this is following ants. With the 5D Mark III I found those little creatures a bit to fast for using autofocus effectively, while using the 1D-X I can follow them around, keep them in focus and get results such as the attached shot of an ant with what you may call herd animals.