Analytically, I'm not sure what to say. I just wrote a long post on Maddon days ago and nothing stuck out to me. He's solid in almost every aspect that we can evaluate without pausing on how much influence he holds. You can't simply look at managers and how their teams have fared in the win-loss column to judge them. In fact, judging them in any matter is pretty difficult. I've tried, and even that rough metric pegged Maddon as a good manager.
Anecdotally, Maddon is perfect. His personality and demeanor are refreshing. Sometimes he's imperfect from a tactical standpoint, and the idea of a manager creating his own stats and using them as something valuable is a tad bit disconcerting, but for the large part, Maddon is fine. It's pretty funny how within three years Maddon went from an awful manager, someone who ran Bill Evers out as his bench coach due to jealousy and his own inability to communicate, and the main force behind the Rays ineptitude to being the manager of the year and being celebrated as the quirkiest manager in the league again.
I don't know the money terms, but I do think a number of teams would have pursued Maddon aggressively this off-season. Ken Rosenthal speculated the Rays don't care to spend too much on field managers, and that makes absolute sense. However, Maddon gels with Andrew Friedman pretty well, and as I'm told; if anyone is going to pick atmosphere over cash, it's Joe Maddon.