I am certainly no expert, but I think that you will be fine laying the tile over the floor as you described it. I layed some tile in my house a few years ago. At that point we were thinking of selling and we layed the tile over the OSB and to date the floor still looks great. My floor area was small (just an entrance) so that might have something to do with this, but basically all you want to make sure is that the floor doesn't sag/shift too much.
As far as the baseboards go, that is the worst part! I agree with the numbering system, but in the end we replaced all of the baseboard because it just didn't come together as well as we hoped (probably because I'm not in the trades!).
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