I would say it doesn't make a ton of sense to start until the end of the season after next, at the end of Smart's first year on his second contract. He and Randle are still so young, and I know his percentages aren't great still, but having attended most Celtics home games this year I believe his shot is getting better and can keep improving until it's respectable. As many have pointed out, if he shot like two 3's a game instead of his routine 4-6 it would be helpful, and that's doable. And as one poster said, he's actually shooting great on corner 3's now, which is a good sign.
I suggest that time because I want to see how much they each cost in the open market, and then to take a year to evaluate whether they are living up to that billing. As they're both 21-23 years old and on cost controlled rookie contracts, I feel there are still too many things in limbo with them. We all know about his intangibles.
I'm honestly more interested in Yab vs Skal, and Jaylen vs Ingram even though we weren't getting Ingram. And depending on who we draft (and I'm assuming here), Fultz vs Ball or Josh Jackson vs Tatum, as those are the 4 guys I've seen and liked (nothing new to pick those guys).