A lot depends on how Ainge values what Olynyk brings. Might rather thin out the guard rotation than renounce the rights on KO. Total wild card right there. Skilled player, works in the system, and size. Tough to just let him walk.
I'm sure someone will correct me if mistaken, but with a $7.7M cap hold, clearing space for a max and then going over it to resign KO is possible, so long as they have the space including the 7.7, not what he actually gets...meaning we can exceed the cap even if we have space and use it elsewhere.
Also depends on how Ainge values Brown, who could be the guy to take AB's starting spot. I'm not so big on Smart, since shooting is so important.
For me, with so many young guards, keeping the veteran Bradley - though still a young veteran - for next season is the preferred route. Then deal with th problems of 2018 in 2018 as far as resignings and the cap.