I'm a long-time poster at the Orioles #1 fan forum, the OriolesHangout, and we are having these sorts of conversations daily. Skubal is scary because of his injury history, so some would not be agreeable to Holliday, Basallo, or Mayo's inclusion in any deal for Skubal, while others feel Skubal is worth the risk and would be agreeable dealing one of the Big Three, plus a lesser prospect or two.
Many of us feel Detroit has little hope to make the playoffs in the next couple of seasons, as currently constructed, but could really benefit with an influx of talent by trading Skubal and Jason Foley. The issue is that Tigers fans and more importantly their front office, may disagree and believe they're a couple of impact free agents away from contention. It's hard to say either way.
FWIW I would be agreeable to trading a package similar to 3B Mayo, LHP Povich, and OF Beavers for Skubal.