But BB wants and expects them to be versatile and I think he drafts with that in mind. (Chung for example, as well as Meriwhether are equally capable as ss or ws)
Ultimatley, there isnt that much difference for an OLB being on the strong side or the weak. I mean in terms of being effective, not how the play presents itself.
In the running game whether you are blocked by the TE, or a pulling G or a FB isn't a matter of different skill sets.
In the passing game we rarely ever have an OLB in man coverage on anyone, so the flat is the flat whether its strong or weak.
I think that part of the reason BB does not flip players is because ultimately there are situations where there is no strength.
One back with 4 wides, or 1 back with 2 TEs has no strong or weak side.
I definitely agree with you on the long term vision for the young players: he wants them to be as versatile as he can make them. That said, it's just unreasonable to expect that versatility to be there in a rookie, especially one who's switching positions. Reminds of what Pepper Johnson was saying about how they involve young players, which is by giving them smaller roles that they can excel in from the get-go, and letting them own those roles while they continue to learn new ones.
If you're expecting a polished, highly versatile starter-caliber OLB from day one, I think that Cunningham is going to disappoint you. It will take him some time to get there, and that doesn't make him a bad pick. It's just an acknowledgement of the fact that switching positions is hard, and Belichick is extremely demanding on his OLBs- they have a lot that they need to be able to do, and there's no way that Cunningham can do all, or even most, of it yet. He'll hopefully get there in time, but he won't be there right away, and almost certainly won't get there this season. If I had to guess, I'd say that this season we'll see him primarily as a weak-side edge rusher, because a) that's a role that leverages the skills that he already has developed, and b) it relies more on athleticism than experience.
In the mean time, Woods is adequate. He's not ideal, and he's definitely a placeholder, but leaving him in there won't kill you (like Eric Alexander does if you leave him in at ILB). For now, that will probably just have to be enough.
I'd also disagree with your assessment on Chung, who just isn't a FS in any sense of the word. The big knock on him has always been that he can't cover; he was atrocious at it last year, and so far the early word out of training camp still isn't great. He's a prototypical strong safety, in many respects. As his recognition skills improve, he'll be able to compensate for his lack of speed by anticipating the play better and taking good angles to the ballcarrier, which goes back to my original point: the versatility that Belichick's looking for needs to be coached into guys. Nobody comes into the league with it. That's why we didn't see much of Chung last year, and will probably see a lot more of him this season. Similarly, I'd be pleasantly surprised if we see a lot of Cunningham outside of a handful of fairly specialized roles, at least until a little later on in the season.