I like all the creativity here and love the fact that even if we were to move someone like Holliday or Westburg to CF, you still cannot get all the top position players currently at AAA or AA in the lineup everyday. That certainly means we still have excess talent that could be used as a trade chip.
Of course, there is also the likelihood someone doesn't pan out due to production or injury. If Mayo were to stick at 3B giving you Mayo, Henderson and Holliday in the infield, I think I would be include to keep Westburg as a super utility guy that still plays most everyday as you flex guys around and keep them fresh with days off. Each of Mayo, Holliday and Henderson can get a day off each week and Westburg can filter in at DH and learn some OF, too, and fill in there. The type of role Ben Zobrist had for a few years, an everyday player without an everyday spot. That also builds in an injury buffer where a single injury anywhere on the field doesn't really hurt.
The other key is Basallo. If he can stick at catcher (even as a part-time catcher), that would be amazing. We all love the Adley/McCann duo, but imagine an Adley/Basallo duo catching and DHing. With both in the lineup nearly everyday, you can carry a third catcher (which would be a luxury available particularly if you have someone in that super utility role).
The options are plentiful which is what makes it so exciting.