My main issue with Ross is that he's under contract for next year, and we already have limited flexibility next summer. Basketball-wise I'd go with Juancho + Nesmith, and I don't think that's crazy for Orlando, personally, since it clears them $8 million in salary next season and gives them a prospect who has a chance to pan out, while the Celtics get someone more usable in their rotation. Ross is an expiring contract next summer, which isn't completely terrible, but I think the Celtics would be better off with more headroom under the apron, which Ross eliminates.
All that said, the C's need to have a good January before making either a Schroder-Ross deal, or any deal for Ross at all.