Huh! This is something I've never really thought too hard about before, but I do have some loose and unformed thoughts!
So the trickster archetype is, broadly, a character who wins by being cunning and tricking the people around them. Typically this is because they are an underdog facing a powerful opponent, and if they face that opponent on the terms that opponent defines, they'll lose. For instance, a physically strong opponent might want to make everything into a contest of raw force; a politically powerful opponent might want to make things a legal battle; a commander of a large army might want to battle on a flat terrain-less battlefield and overpower the smaller enemy force through raw numbers; etc etc.
A trickster doesn't have the raw power to make a scenario happen. Instead, they achieve that scenario by making other characters make it happen, usually by misleading them into thinking it'll have some other outcome they want.
A classic example of this is found in a Brer Rabbit story where Brer Rabbit has been snatched by Brer Fox, and Brer Rabbit begs and pleads with him to not throw him into that briar patch, oh the torment he would experience in that briar patch would be unimaginable, drowning or burning would be bad but still better than that briar patch. Brer Fox naturally throws him into the briar patch, at which point Brer Rabbit vanishes into the underbrush and helpfully clarifies that he was born and bred in a briar patch. He was unable to escape through his own power, so instead he convinced Brer Fox that yeeting him into the briar patch would give Brer Fox something he wanted (Brer Rabbit's unimaginable torment) when in actuality it gave Brer Rabbit exactly the cover he needed to escape. It only worked because Brer Rabbit understood that Brer Fox was fundamentally not just hungry, he was cruel.
Tricksters usually achieve victory through lying, stealing, sneaking around and generally being dishonest. These are usually not seen as heroic traits, but the trickster hero is an archetype of character who is broadly heroic - and uses trickster tactics to win. It's an interesting suite of character traits to balance. In order to make a trickster heroic, them being the underdog usually needs to be played up. It's not really easy to root for someone with power to manipulate people for their own ends, but it's easy to root for someone scrappy and underleveled to manage to gumption their way to a victory over a broadly superior opponent.
A sympathetic trickster usually isn't someone who picks fights. Trouble comes to them, and then they need to find a way to escape or stop it. This is the paradigm that makes Bugs Bunny work as a trickster hero - he starts off basically every adventure minding his own business, and when someone comes around with a blunderbuss and a hankering for rabbit stew, their actions are what prompts him to unleash absolute hell on them by using toon physics and trapping them in ironclad social conventions to completely unbalance them until they're eventually defeated.
If we see a big, loud, powerful jerk try to stomp on someone small and innocuous, we're inclined to root for the small and innocuous person. This setup makes us very eager to see the small and innocuous person use tricks and shenanigans to make a fool of the powerful jerk, and it automatically makes us more okay with the sympathetic character doing on-paper unheroic things like lies and manipulation as long as they're doing them to someone we're primed to dislike.
So trickster heroes are usually fundamentally reactive characters. Something bad happens and they respond by unleashing hell. Another easy way to make a character instantly more heroic is to give them an even weaker, even more sympathetic character to protect or assist. Thus, many trickster heroes have a suite of supporting characters they're protecting who are not tricksters by nature, and are instead just there to be endangered or bullied by Nasty Mean Powerful People. Our trickster heroes stepping in to aid and protect other people thus gives their actions an even more heroic cast, because not only are they reactive to an outside threat, they're selflessly reactive.
This is the framing that's used in Leverage, where every episode has a victim of the week being cruelly taken advantage of by a jerkass of the week, at which point our team of liars, grifters and thieves roll up to ply their trade on the jerkass and award the spoils of war to the victim of the week. Because the person they're tricking is proven unequivocally to be truly awful and completely insulated from legal consequence a solid 98% of the time, we don't feel particularly bad seeing our team of heroes manipulate, gaslight and eventually absolutely destroy them over the course of a crisp 40 minutes. The vileness of the villain combos with the innocent powerlessness of the person they're advocating for, and thus their assorted unheroic qualities become reframed as absolutely heroic due to the circumstances under which they use them.
Crucial to the formula is the horrendous nastiness of the villain of the week, because if we were even kind of sympathetic to them, the schemes of the protagonists would be kinda scary. They are very good at quickly getting the bad guy to trust them and then taking apart everything they've built, and that's only fun to watch if the audience is 100% sure the villain deserves it and is not going to spend too much time thinking "wow, it would be terrifying if that happened to me." The fact that our heroes almost always take them down simply by leveraging (heh) the bad guy's badness is a big part of what makes the formula work. Almost every episode is functionally similar to a Briar Patch scenario - "oh gosh I sure hope no SOULLESS CAPITALIST VAMPIRES take advantage of how MANIPULABLE I am to try and get my MONEY and/or VALUABLES", and then the villain's own established cruelty cascades into their downfall when it runs into the dominos our heroes have set up to expose them. And that does a lot to make the audience sympathize with a crew of four self-admitted terrible people (and Hardison, who's an angel and we're delighted to have him)
Another way to get the audience to root for a potentially nonstandard protagonist is to set them up against a villain who is smug. Smugness is a very dangerous trait for any character to have, because it primes the audience to want to see them break. A villain who thinks they are too powerful or too strong or too smart to be defeated has the audience immediately rooting for them to be proven wrong just so they can watch the expression on their face. This is the strat they use in Columbo.
Every Columbo villain is rich and powerful and very insulated from legal consequences, and we start every episode seeing them arrange and execute an attempt at a perfect murder. We know from the start how they did it and usually why, and because they are smug - they are almost never regretful or reluctant - we become invested in seeing how Columbo figures out what they did, how they did it, and how he can prove it and get them arrested. Columbo is a nonstandard kind of trickster hero, because he is deeply and fundamentally a Lawful Good archetype, but he is also a very casual liar. The only time the audience sees Columbo almost certainly telling the truth is when he's dealing with background characters, his fellow policemen or his dog, or when he's by himself silently putting the pieces together; at all other points in the episode he will typically conceal how much he knows, how he knows what he knows and why he's asking specific probing questions. The audience has a tremendous amount of dramatic irony in terms of information about the perfect murder Columbo has to disassemble; we'll see Columbo zero in on exactly the one small detail that pokes a hole in the supposed airtight alibi, but instead of saying "I think you killed them and I am determined to prove it" he'll dance around why he's focusing on those details - just curiosity, just a desire for completeness, his superiors told him to continue the case and he doesn't know why, his wife is just such a big fan of their work, etc etc.
As a rule, the first time in any given episode that Columbo admits he's suspicious of the villain is the beginning of the last scene of the episode when he proves that they did it and they subsequently surrender. When Columbo is dealing with the villain, absolutely nothing he says can be trusted until that final scene - and it's a rare treat to get a glimpse of Columbo showing an honest emotion, especially something like genuine fury. Most of the time he maintains a very harmless and affable attitude, but sometimes when the villains are very smug and they know he's suspicious of them but can't prove anything yet, his righteous anger peeks through and we see why he does this.
He's a trickster hero because he can't unravel the case, the villain's motivation and the shape of the crime if the villain knows everything he knows and can correspondingly keep up with him. But he is 100% committed to exposing the truth of the situation and making the murderer face justice. Their perfect alibi is supposed to protect them from everything, but it's their confidence and certainty that they could never be caught that Columbo leverages to win. They never know entirely what to make of him, and he's never wholly honest with them - and with the audience - until the very end of the episode. It's good, cathartic payoff to an episode's worth of lies and manipulation from both main players, and it's always fun to see the non-smug party on the side of justice come out on top.
Some trickster heroes are more like standard heroes with trickster tendencies that occasionally surface. These guys are usually pretty straightforward, but in a pinch they can bust out a surprisingly cunning scheme or two - one such moment hits at the climax of Across the Spider-Verse, and it's a great moment of characterization for Miles, who has thus far been a pretty typically heroic guy who has unfortunately spent the entire movie thus far being lied to by people he trusted. It kicks off an enormously long and complicated chase sequence that takes the entire spider-community out of the home base chasing him through an absolutely massive complex and eventually onto a space elevator. It's such a fluid scene, you kind of just accept that it's a desperate chase sequence - Miles is just running. It doesn't occur to the other spider-people that Miles might have a plan beyond running until he basically tells Miguel that, hey, he did just get every other spider-person out of the facility that has the portal to get him home. He wasn't just running away, he was luring everybody away so he can leave.
And this moment is fantastic on a meta-level, because Spider-Man is traditionally a bit of a trickster hero. Most of his enemies are able to physically outpace him, and he needs to use mobility and strategy to take them down, often luring them into environments that work against them - like a fun moment in Spectacular Spider-Man where Spidey defeats the Rhino by luring him into a steam tunnel and basically giving him heatstroke through his armor plating. But because the entire core theme of this movie is "Miles isn't a real Spider-Man," it literally doesn't seem to occur to the other spider-people that Miles's seemingly panicked running might be him pulling a Spider-Man on them. We're so used to being in Miles's head and knowing when he's got a plan or a ploy that this is a very fun moment to watch. He's successfully deceived an entire army of spider-people, and the audience is just as blindsided as Miguel - and a little less electrocuted, so it's a lot more fun for us.
So yea, trickster heroes are a fun little space of character, but you gotta be careful to put them in the right kind of situation, lest their fundamental dishonesty come across as alarming rather than extremely rad.
