
TGMaxMaxer |
Skulking slayer (H-Orc rogue archetype) and Lore Warden or Cad fighter archetype, Maneuver Master Monk.
Skulking Slayer gets to use a dirty trick/steal maneuver anytime they can sneak, and get a bonus to them equal to their sneak dice.
Lore warden get a flat +2 at 3, another at 7, and another at 11, total of +6, including combat expertise for free at 2. and feats to take the imp/greater for them.
Cad gets to count dirty trick, disarm and steal +1@2, +1 every 4 after that. (6, 10, 14). Also get to use trick as immediate at 7, Feat: Catch Off Guard for free.
Maneuver Master monk gets to take maneuver feats as bonus, and gets to stack maneuvers in a Flurry, so good choice as well.
So, any mix/match of those, altho i'm not familiar with gestalt games.

TGMaxMaxer |
I like the Skulking slayer, instead, if you have to take a mid BAB class to try and get manuevers with, one that gets extra sneak while you do it (blinded being a valid condition to dirty trick with, one of the most useful actually and makes target flat footed in addition to other conditions) is my fav.
As far as the dirty fighter, the only thing he really gets is the double/triple trick at 13/17.
The +2 at 5 is worse than the LW at 3, and the LW applies to any combat maneuver, and the dirty trick in place of an attack at level 9 is done by the slayer at level 1(if you could sneak attack), MM Monk at 1(-2 for it in addition to reg attack) or just by taking quick dirty trick feat at BAB +6.
If you're going to get to level 13+ reliably, then this would be another valid choice, but I think you could do all the same things at the same or higher bonuses at a lower level with some creative design.

Atarlost |
MM's maneuvers are at -2, -7, and -12. Lore Wardens are at +2 up to +8 except at very low levels. Monk gets to roll more times, but lore warden gets to land maneuvers more.
SS/MM is going to suffer the "joys" of multiclassing two medium BAB classes.
If you're ever going to land maneuvers at high levels Lore Warden is the only option. CMD scales too fast.

KutuluKultist |

Maneuver Master is almost mandatory for reasons of action economy.
For any maneuver build at all, I'd recommend MM 1/Lore Warden x. MM2 has some justification, but each level of MM delays the next CMB bonus from lore warden, which you really need.
Hence I would add a second level of MM at after Lore Warden 7 the earliest.

Atarlost |
Oh, another gestalt thread. I should read the OP next time.
Lore Warden, as above, with Vivisectionist Alchemist. You can pick up the quick dirty trick feat to blind someone with a dirty trick in place of your first attack and then sneak attack them with your iteratives, all the while using mutagen to boost your CMB even higher.