What this hiring says is that BB is not looking to fill a room full of "yes" men. Every good manager wants to hire people that will provide alternative viewpoints and when appropriate, question his/her decisions in a professional manner. In Reese, BB has that person who is comfortable enough to challenge and question BB's decisions or offer council. Additionally, BB is comfortable enough with Reese and obviously has a deep amount of respect for his footbal knowledge.
In terms of Reese's drafting record, IMO it's more than good. No one hits home runs 100% of the time. Caserio will work with Reese to set the board and BB will pick the players.
As far as the cap goes, there is already a system and a financial philosophy in place. With the Krafts and BB's already-established financial structure prooven to work, I don't think they will give Reese carte-blanche with their cap structure. He will work the contracts under pre-defined operating parameters.
As a whole, IMO this is an outstanding move.