With the upcoming release of the advanced class guide, I have again found myself turning to the idea of a halfling monk or brawler. I really want to do this. Is there any way to get around the penalties for small size with combat maneuvers?
There is the Halfling Underfoot Adept archetype for the Monk class. Fun and cool, it also may or may not stack with the Maneuver Master archetype, depending on GM interpretation (MM changes what feats you can take as a bonus feat at 1st level, UA replaces your bonus feat). I'd let it happen, as would most GMs I would wager, but there is that risk.
Also, you can just focus on disarming, sundering and dirty tricks. You still get -1 to CMB for being small, but you can do those as well as a larger PC.
You should give Kobold Style feats a look as well.
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The penalty for small size is only a -1 adjustment - BUT you also have a -1 for effective STR (most small races have a -2 STR penalty) and you have to deal with the rules for trip, if you intend to go that route, which say you can only trip creatures one size category larger than yourself. In order to be effective at tripping when most of the monsters are Large or larger, you will need to find a way around that.
Grappling is also tough for DEX-based characters, unless they have some way to not take the -4 penalty to DEX when you are grappled. When that is stacked with the -2 to hit from being grappled, you will have a heck of a time making those Grapple checks. 4 Levels of Tetori helps with this piece.
Can it be done - and will it be fun? Yes to both, but it is gong to take some effort to make it work effectively.
The penalty for small size is only a -1 adjustment - BUT you also have a -1 for effective STR (most small races have a -2 STR penalty) and you have to deal with the rules for trip, if you intend to go that route, which say you can only trip creatures one size category larger than yourself. In order to be effective at tripping when most of the monsters are Large or larger, you will need to find a way around that.
Grappling is also tough for DEX-based characters, unless they have some way to not take the -4 penalty to DEX when you are grappled. When that is stacked with the -2 to hit from being grappled, you will have a heck of a time making those Grapple checks. 4 Levels of Tetori helps with this piece.
Can it be done - and will it be fun? Yes to both, but it is gong to take some effort to make it work effectively.
You can easily grapple larger opponents with the Kobold Style featline... you need to knock them prone first, but that is part of the fun.
If you really want a strong argument for them stacking, look at the Quingong Archetype, which Devs have said stacks with all others because of the word "May" in it's choices.
Maneuver Master uses the same "may" in the bonus feats section,
Bonus Feat: In addition to normal monk bonus feats, a maneuver master may select any Improved combat maneuver feat (such as Improved Overrun) as a bonus feat. At 6th level and above, he may select any Greater combat maneuver feat (such as Greater Grapple) as a bonus feat. At 10th level and above, he may select any maneuver Strike feat (such as Tripping Strike) as a bonus feat.Unlike many others, it does not say it replaces a monks normal bonus feats, just adds options on top of the normal list that they may choose.
It's a small distinction, but the same distinction that allows Quingong to function in addition to all the rest.
This is actually a super cool justification besides "come on, man, don't be stupid about it."
By the way, I'd focus on Dirty Tricks in addition to Trips if you want to go the Underfoot Adept route. You're not getting screwed by size changes and Dirty Tricks is a pretty good combat maneuver besides.