Team Rocket as a criminal organization is obviously kid friendly compared to the ruthlessness of real life illegal syndicates. However there is no doubt that crime will exist in a Pokemon world; the superpowers Pokemon possess makes it easy to perform illegal activities swiftly and efficiently.
The rules of crime in the Pokemon world might have some changes. Many people joke about how Team Rocket never use guns and instead have Pokemon Battles. However let's assume that Meowth has Psyduck at gunpoint: what's stopping Psyduck from using Psychic to turn the gun at Meowth? How would a gunman be a threat to a Golem's literally rock hard body? Gun ownership would still exist; it just wouldn't be very useful. Alakazam alone can use Teleport, Barrier, Double Team (TM), Thief (TM) or the aforementioned Psychic to make guns irrelevant to it; and that's assuming Alakazam's high Speed doesn't already take down the gunman before that.
But because of how dangerous Pokemon are; I don't see a scenario where Ash and his tweenager friends are allowed to walk alone for months and years away from home. The games acknowledge that children trainers are going to have Pokemon that are at best Level 10; this would be realistic, especially if these same children view their Pokemon as pets rather than training them for battle. So Team Rocket members could easily prey on inferior Pokemon Trainers to steal from them.
Sleep and Paralysis moves will be the most efficient at ambushing humans and Pokemon alike (without doing something as extreme as actual assault or murder). In regards to Gen 1: Jolteon and Electrode has the speed to effectively strike first and both can learn Thunder Wave. Aerodactyl is also large enough to lift small Pokemon and some humans while also having high speed. Gengar and other Ghost Pokemon are confirmed to have some traits like invisibility, phasing, hiding in shadows, and various methods to flinch or scare their foes; which will be very useful indeed. Flying, teleporting or digging Pokemon in general will make for easy getaways.
The Johto games do present a realistically morbid example of Pokemon poaching; when Team Rocket hunt Slowpokes for their tails. This would make sense, especially since Slowpoke are extremely vulnerable due to their slow speed and infamous stupidity. Parasect might be similarly exploited; also having slow speed and a somewhat valuable item (Tiny Mushroom), while also possessing various powders and spores that could be weaponized by Team Rocket.
I also want to mention a recent Dorkly episode where they question why Team Rocket goons follow the '6 Pokemon Team' limit despite being criminals. The anime does show Ash's Krabby being automatically sent to the 'PC' when Ash went beyond his 6 Pokemon limit, despite Ash wanting to have Krabby stay on his team (Krabby/Kingler would spend the rest of his life as one of Ash's most forgettable and neglected Pokemon). However this is only in regards to Pokemon caught in Pokeballs; there is a possibility that taming Pokemon that have no Pokeballs (aka Walking Pokemon) could bypass the software by not involving anything to do with the PC mechanics. Keep in mind that Professor Oak is legally allowed to take care of Ash's Pokemon, despite going beyond this limit (at least we know Kingler is in good hands). Although with that said; I would assume that Team Rocket would launch raids on Oak's lab or attempt to hack PCs to steal Pokemon.
Home insurance, will be a NIGHTMARE. Arson, both intentional and unintentional, will be RAMPANT. There are several Pokemon confirmed to be strong enough to destroy houses, and plenty of fire types to burn everything down. Famine could also be an issue if infamously gluttonous Pokemon like Snorlax or highly toxic Pokemon like Muk infest farmlands. But Repel only works on Wild Pokemon; it doesn't affect humans, and you can't use Repel every minute of every day without it being expensive. Team Rocket meanwhile can form Protection Rackets by threatening to destroy entire towns overnight; something which most Dragon Pokemon can do by themselves. Infrastructure and architecture would need to somehow be able to survive or resist these absurd Pokemon on a daily basis. I would not be safe in my house when there are multiple Ghost Pokemon confirmed to be invisible, able to phase through objects, teleport, and most importantly: kill, steal or eat human souls in some way shape or form.
Now we must look at the classical Poke-Waifu: Officer Jenny. Yes, Growlithe is a reasonable K-9 unit for a police officer; but there is no way Jenny would survive long with just one single Growlithe, or even an Arcanine: she is going to need a full squad. Since police in real life have rights, legal abilities and freedoms that regular citizens don't (the ability to arrest, carry a gun, use lethal force) then it is possible that Jenny would be given some legal tools to assist her; perhaps being allowed more than 6 Pokemon on her team. A possible requirement for officers is to have high level Pokemon so that they can overpower criminals more effectively: which is shown in the Pokemon lore when Lance (an Elite Four member) is actively fighting Team Rocket during the events of the Red Gyarados in Johto (or maybe Lance wanted to catch the shiny pokemon, which he did in the Anime). Security Guards might also need to be above average Pokemon Trainers, maybe: Snorlax would be a great bouncer perhaps. Jigglypuff would be excellent riot control if it could just Sing everyone to sleep; but Stun Spore or the putrid stench of a Muk should work too. No surprise that a pokemon like Blastoise (who knows Hydropump and Rain Dance) would work well for fire fighting (and maybe crowd control too; assuming it doesn't use its "punching holes through thick steel" water jets).
And now for some Pre-Crime/Minority Report speculation. There is a Pokemon move known as Mind Reader: if this is literal, that means that solving crimes would be done in an instant. Lying under oath would be physically impossible in a courtroom. That said, it is also possible for these same Pokemon to just… lie: that would create one extreme scenario of legal corruption indeed.