I think there's a plan in terms of the style of play the team wants.
Where my doubts come up is there seems to be a prevarication on whether they're going for it or building for the future. Take the Aiyuk pursuit. That feels very win now. But it felt kind of half-hearted. Lowball offer to the 49ers, lowball offer to Aiyuk (per Breer - that's the bit that really shook me). Or the Wilson move, which was very much sold as win now, got to see if there's a window there.
We'll see how it plays out this off-season.
There are some real questions about the coaching too.
I think they are always trying to "win now", but the moves they are making are setting them up for the future like Jones (assuming he improves), Fantanu, Benton, Frazier, etc. Those are the type of guys should be here the next 10+ years.
Wilson, Fields, even Queen given his team friendly deal....those are "fell into their lap" type of deals IMO. I think lowballing Aiyuk was, too. If you can get a guy that good for that cheap, take it. He'll probably be good for 5+ years so he'll still be here for their "window". They didn't, so OK. I think that's why they probably didn't get Adams, Krupp, etc., too, because they were lowballing. I think that's fine. Those ARE "win now" moves given their age. I don't think the Steelers are quite there yet to give up enough to make those deals.
I'm pretty indifferent on Harris, but that was clearly a win now move. I don't really see any of the moves Khan has made as that type of deal with the exception of maybe JPJ given how short CB careers are. Even then though, some people had the Steelers taking him with their 17th OV (roughly I forget exactly where they were picking) and they got him at 32. So that could even be a "fell into their lap" type of move .
I think the next 2-3 years are "win now", though, with Watt, Heyward, Fitz, etc. getting up there. Resign Wilson. Sign Higgins and/or draft a WR in the 1st. Get Fantanu back. Maybe resign Daniels. Maybe Roman Wilson will make an impact. Jones, Frazier, Benton, etc. getting another year of experience. I think it's all there except.....
....I don't know that the coaching is.