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I may have gotten carried away :wink: so, I edited down to one question :blush:
I've heard from several attorneys with varying opinions and strategies. I'd really appreciate feedback and/or opinions from experienced domainers on this issue.
The only people who might be able to offer reliable feedback about what the USPTO is/is not likely to do are patent or trademark attorneys who have experience filing Trademark Registration Applications. Although the people who post to this forum have a wealth of knowledge on domain names and other topics, you are doing yourself a disservice if you ask for non-legal opinions on this particular subject (trademark registration).
I see you say you have heard from several attorneys. I would suggest you go with one of their opinions (keeping in mind of course that they are also unable to predict what the USPTO will do with absolute certainty).