I don't see it that way. First, any big contract you offer an NBA veteran has the potential to end up being a bad contract. It's a high risk business. OTH, I'd rather see the team take a risk on a player who has the potential to be a real difference maker over giving contracts to the types of mid-level talent that are otherwise likely to be available to the team in the next few years. The Blazers are stuck in mediocre-ville at the moment. No chance at another lottery pick. No cap space to sign a significant free agent, plus the lack of big market appeal to woo such a talent. Not enough assets to have a realistic shot at a trade for a franchise-level player.
Cho can tinker with the role players and improve the Blazers chances of winning a first round series, but I just don't see anything out there that is realistically obtainable that would put the Blazers into title contention with the single exception of re-signing Oden and having him able to contribute at a significant level for a few years. As long as the medical experts are giving him something close to a green light, I'd say it would be irresponsible to let Oden get away. I'm not sure that you have to go all-in on a max-level contract in order to retain Oden, but I'd assume that Cho has a much better idea about that than I do.