I think a lot of people are underestimating the worst case scenario with Upshaw's addiction. I've heard a lot of "If things go south, just cut him".
If you've ever worked with someone who has a chemical dependency, you know things don't just go smoothly until there is one big blowup.
IF things go south, it will likely be pretty complicated. He'll be late for practice, miss film session(s), be late for a team flight, get in a fight during practice, be physically present but mentally vacant, and on and on. And you can't just test him every day and cut him if he tests positive, before any problems arise. Drug testing is collectively bargained and I don't believe the number and frequency of allowable tests is unlimited.
And the thing is, if he's late for a practice, you don't cut him for that. That's why you frequently hear stories when an athlete implodes that they had been a problem in the locker room for a while.
Regardless of where he ends up, I hope for his own sake that he becomes a model citizen. My whole point is that I believe the potential downside is much worse than some think. It's not as easy as "just cut him". He could do some damage before he gets cut.
Having said that, I'm all for taking him at 33.
To me it comes down to whether Brad and the staff think it will be worth dealing with the potential problems. Because ultimately, the coaching staff will be the ones who have to deal with it (as well as his teammates).