Celtics need to stop chasing guys who are already established and starting getting guys on the upswing. Christian Woods is one of those players. He has a cheap contract and he's trapped on a rebuilding team. He's an agile, athletic big, who can shoot as well as drive the ball. I'd trade TimeLord, Nesmith, a protected 1st for him. I don't think resigning him would be an issue and he fits with the Jays timeline.
You realize there is a contradiction in your thought pattern here, right? Christian Wood, young guy on the upswing, but you want to trade Timelord to get him, an even younger guy on the upswing.
Wood fits into out TPE, so that and two picks(1st and a highly protected 1st that converts to 2 seconds). Or Juancho, Freedom and Nesmith with a first works also. Two expiring contracts, a prospect and a pick seems reasonable.
If Wood goes on the block though, I imagine those things won't be enough. Several playoff bound teams will be jumping all over the place in a bidding war for Wood.