Random thoughts..
Can Messi and Maradona work together? probably but is it a great fit? no, highly doubtful. Both have exceptional football IQ and are very selfless on the pitch, they love making great assists almost as much as they love going for goal. The way I see them working in tandem is if we assume it is a prime Diego of 1986 and a younger version of Messi ala 2008/09, on the verge of greatness but has all the dribbling speed, constant running threat in the final third albeit not being played as a false 9 but playing out wise.. so not quite at his best, but in a position he is more than comfortable in and at his physical peak in terms of being a direct threat. Sort of like prime Dinho but as a 10 combining with that young peak Messi.
Gerets and Ziege help provide width which is important, in that even if they step on each others toes and there is an abundance of threat through the centre, there is always the easy out ball to full backs with good thrust out wide, which is similar to Barca under Pep. We had Alves and Abidal, helping to provide width and allowing Iniesta and Messi the room to co-operate harmoniously rather than getting in each others way. That said, one is a LAM and the other a RW/F9 whereas Diego and Messi like roaming down the right and cutting in. Diego does however roam on both sides of the pitch so he'll have to be careful to ensure he isn't always on same side of pitch as Messi.
With regards to the other side.. it is arguable that Henry and Ronaldo aren't an ideal partnership either. Both are runners with the ball, all-rounders granted but I can see Henry being a tad intimidated with R9 as a partner. He was at his best when he felt special and the main man.. also I'd have Henry as the slightly deeper one on the graphic if you are going to pair them. On paper it looks a great front 6, but I do question if players like Beckham and Gento are perfect fits for an Henry. He's the one who looks an odd fit in that front 6, everyone else looks ideal though Effenberg and Matthaus are not a great match either in practice. Effenberg again likes to be the main man and I think he would hate being partnered with Matthaus.