This has been a really useful thread for me: it's settled, an upcoming mission will be to thoroughly discredit Teemo through a campaign of misinformation, record corruption, etc.
My players have avoided further interactions with Teemo by being captured by Zyggerian slavers. Imagine Trex making a selfie with a big thumbs up in the foreground, with the PCs kneeling in chains behind him, and Teemo's booming laughter at the picture. You can bet that the players are sure to want to make amends for this indignity.
After the Zyggerians are dealt with, ideally one of the friends/contacts they make will also have a beef with Teemo and will suggest reprisals. I'm still fleshing out the idea, but I figure this could involve 3-4 sessions:
- identify a few spice shipments and a likely stopovers, film the "crew" swapping out spice crates for frozen nerf steaks, and hack the ship logs to make them look like they've been poorly hacked to cover up other destinations where the real spice was delivered. Involves Stealth, Streetwise, Deception, Athletics, Skulduggery, Computers, and perhaps many other skills as the crew and captain are "diverted", gotten drunk, etc.
- show a crude video of "Teemo" laughing as he intends to screw over one of his customers (or a rival Hutt). I'm sure the players will have fights over who gets to wear the Hutt suit. Deception, Charm, Coercion, Coordination, Leadership, Knowledge (Xenology, Streetwise, Underworld)
- hack into a BOSS node* to plant the corrupted ship logs and sync things up. Involves a physical insertion onto the site, ideally undetected. Stun guns and masks are a must. Computers and combat seem likely, along with Stealth and Skulduggery, etc
- hack the holonet* so the video looks like it was posted from inside Teemo's palace. Maybe make it look like Trex is double-dealing. Also involves physical insertion, so ditto on the skills.
Ideally every stage will have broad enough requirements to involve every PC.
* I use RL analogues for a general sense of how the holonet works and how prevalent it is. WEG's work and views of the holonet were fine for their day, before anyone heard of the internet and understood how ubiquitous it would become, but TCW blows it apart.