The poker game got me thinking. Most of us see Pintsize as Annoying Wacky Hijinks personified - an unleashed id. But a lot of the more overtly jerkass-flavored things he's done have had interesting side-effects....they've caused things to change for the better for other cast members.
The most immediate to memory examples I can think of are both connected to the current long arc - Faye was desperate for work, had just gotten nomphed on for falling off the wagon, and suddenly here's Pintsize offering legally questionable work in an occupation that's a perfect fit for Faye's personality and skills, in the sketchiest way possible. He does everything he can to make the connection seem as sleazy as possible...but he still hand-set Faye into a possibly lifesaving job.
Then, when May was scraping to get the last cash needed to have the temp fix on her head properly finished, here's Pintsize offering her a little cash to sit on his face, then a little to let him sit on HER face...and then a bidding war with Marten to add almost double what Pintsize just paid May, making the repair cost a lot less fraught for May. Sleazy on the first glance...except they're both AIs in neuter bodies, and they BOTH seemed mostly bored rather than disturbed by it, and it's high odds even if Pintsize had won the bidding war, May would have pointed out that sans Marten's consent, she'd be jailbound. Following this thread further, May immediately gets her repair job... on a day when Roko's on-duty watching the park. The tensions of Roko poking her nose in cause Corpse Witch to threaten May...which causes Faye to do her standard action on anyone who legitimately threatens her friends, leading into the whole mess that finishes Corpse Witch and frees Bubbles.
If you really, really think about the things Pintsize has done, even in failing to transgress he's done things that arguably benefitted the cast. Triggering Marten's Loom Of Doom in pre-emptive defense of Claire is a good example - he caused no harm and nudged Marten into being a bit more visibly assertive. This arguably has helped that relationship. The similar incident with Bubbles' houseplant Arthur comes to mind as well.
Another point in favor of this way of thinking is the Vespavenger - while it's an admittedly silly bit in context of the modern style and storylines, it still shows something: Pintsize is willing to actively, decisively put himself in harm's way for the cast. This is not a small thing, and when thought of in these terms, his transgressiveness could be seen as willingness to suffer harm to improve the lives of others, masqueraded under a jester's antics. Even the "replacement Dora" incident can be viewed in this context - a kick in Marten's brain, forcing him to examine the relationship the hard way, making him question if it was a truly mutual thing or just him going along to get along and/or get some, all nicely hidden by the crudity of the 'gesture'.
Following this, consider how many times Pintsize has faced what might be considered an AI's chief fear - deactivation. Being manually shut down, in a way that prevents him from kicking back on. Externally being rendered non-conscious is TERRIFYING to most people, and I honestly can't imagine it being any less so for an AI. Pintsize has, on 5 occasions by my count and feel free to correct me if I've missed one, been forcibly shut off. Four of those were arguably medical emergency equivalents - cake batter, de-lasering, de-Brit'ing, and de-virusing. The fifth was the result of whatever happened between him and Faye the night she nearly drank herself to death.
Really think about that. Faye was arguably into diminished capacity territory, a mindset where right and wrong just do not scan at all to the subject. She cared about drinking the pain away, and nothing else. Pintsize did something that made her do what nobody other than Marten has ever done, and Marten only in case of arguably dire emergency. The general consensus amongst forumgoers is he tried to stop her, and she reacted to that by stopping HIM. Pintsize, whatever his affect, is not dumb. He HAD to know that if she was that openly, visibly out of control, trying to step in in any way would be like tapdancing on an anti-tank mine.
He still did it. He has never called her to account for her actions, either. That says something about a person.
Shred my mini-novel at your leisure, folks!