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So, I have three things in mind that I'd love to see folded into a singer character*, and I would like some extra minds to help me mull over the possibilities.
1) Mouser Cavalier cavalier. oops. Thanks, avr. You can get into your foe's square pretty easily (they just have to miss you) and you debuff them.
2) Monkey Shine style feat. Probably acquired via a two level dip into Master of Many Styles Monk. Even more in-your-space goodness, but buffing you this time!
3) Vexing Dodger Unchained Rogue. There is some fuzziness on whether you're technically in your opponents square, but it fits the theme of climbing on/around/over/etc. I'd like to incorporate this too as it's a nice class-based way to "stick" to your foe.
So, I have a few different builds floating around in my head, but most place the majority of the time in the Rogue. This character would be joining the game at 5, so I can get away with starter level awkwardness and get all my dips in early. With my current build, mouser 1/ MoMS 2/ Vexer 2+, I'm one level away from dex-to-damage, but that's ok. My main job would be to get in a foe's square and make life super difficult for them while my friends go to town.
Have any of you come up with builds that utilize any of these, or all three? I'd love to see them!
*I recognize that this is probably going to be a sub-optimal/weird/awkward build. That's ok. I'm just looking for maximizing being in a foe's space and seeing just how hard we can push that angle. Some parts of this character, like the swashbuckler's finesse thing and the rogue's overlap a bit. I'm ok with that too. Again, just seeing how far we can push being in a foe's square(s).

avr |

Mouser swashbuckler not cavalier. MoMS monk was nerfed years ago - you can't get the second feat in a style chain from it given a 2-level dip.
The tangle feet or tumbling upset feats might fit your theme. Or sliding dash if you can wait until 10th level or if you can figure out what class feature they mean.