Not very complicated. The question isn't whether to trade Dozier or not, but rather what to do with Dozier until the Twins receive an offer worth consideration. I'd move Dozier to LF next spring, install Polanco and Escobar as the everday 2B and SS, respectively and prioritize Gordon's development. Dozier can't be worse than Grossman defensively and he should continue to hit wherever he plays thus increasing his trade value.
Why make an effort to trade Plouffe now when his value is down? A quick review of other MLB rosters yields a multitude of players the Twins traded prematurely, just to "move on." To move on where exactly? How'd that work out? It's easy to deceive oneself into thinking one is a master trader, but there's always someone on the other side who just might know more than you. Oftentimes, patience is underrated.