@Pinelark:
I think Bartholomew Bear takes my point to a little bit of an extreme (though if you really feel that way it's cool Bear :P). My main concern isn't how Doflamingo's acted up until now, it's his threat level now that we're here.
I thought overall his plan wasn't bad, and yeah lots of villains do the whole "i won't underestimate" bit, but who can really plan for the Strawhats? Especially when Doflamingo has never had access to intel covering the "tactics" (I use that word incredibly loosely) of their entire group?
But his threat level now is the problem. So what if Doflamingo beats Luffy? What happens then? Does a weakened Doflamingo then get stopped by Sabo or Fujitora? My issue here is outside of Luffy's possible death, there doesn't seem to be any repercussions for what might happen if Doflamingo actually wins. Kyros makes a big deal about "will this country return to darkness?", but no. It won't. It can't. Doflamingo's entire family with the exception of Trebol has been defeated, quite thoroughly. I'm hard pressed to believe Dofla and Trebol can win back the island even if Dofla beats Luffy.
The main problem is that Oda has decided to make the anti-Aizen with Dofla, Trébol and co. They know what they know, nothing else, they don't know what they realistically have no chance of knowing, and when surprise things happen. . .well, they just happen. No one has warned them about Mansherry being no longer their captive, so they shrug off all damage caused to both the officers and the Factory cause they trully believe they'll reset them. We know they don't have Mansherry anymore, and so when they show confidence based on things we, the readers, know are no longer on their possession, it doesn't feel right. . .even though it's actually a pretty honest approach to villainy.
When Doflamingo was 100% sure no one would enter the underground port or that Luffy was clearly fighting in the Colosseum, he was perfectly allowed to think that. We, the readers, knew he was wrong from like 5-10 chapters before that, so those moments didn't feel "right".
I guess the solution would've been to have a set of fail-proof measures in case things went awry, which in the end happened to be the birdcage and. . .not much else, or just don't show the villains with a smug smile telling the heroes to despair when we knew a solution to the conflict was well underway without the main villain knowing.
And finally, yeah, Sabo and Fujitora in there is total overkill for any aspiration Dofla might have right now. Again, Mansherry must've been a pivotal part of their aspirations, cause I guess Doffy + the entire family vs. Fuji and Sabo IS also a bit too much, I guess. And in fact, I don't think they factor Sabo as a problem, more like marines and revos will eliminate each other out, which almost happened. The marines did get slightly decimated during their conflict with Sabo.
But, yeah, I think at the very least Doflamingo himself has managed to stay as a powerful threat, at least at a physical level, and the family as a whole is more memorable than people give it credit.