Skidd's is a favourine of mine but i have tonnes of trouble making him work on Hard difficulty.

At times I wonder if i'm just bad, if Skidd's is bad, or if it's just because I keep getting Paranoia and Indebted on him.

The things i've tried to include:

Leo + Stealth + XP-Pickpocket+ Lockpicks + Backstab & XP-Sneak attack. In addition I got Machette and lonewolf and a supplementary set of cheap cheap cards (Mostly skills). I.E a Skidd's that can protect himself but mostly relies on agility and rouge cards to stay mobile and pick up clues

Combat Skidds, Typewriter + Combat training + Lone Wolf + Leo + Machette + a lean shoestring deck that costs barely anything. A combat Skidd's that deals with life by beating down his woes.

What are your experiences with Skidds? Have you made him work (On hard)?

I'm currently playing Dunwich (standard) two-handed with Skids and Akachi, and they're doing fantastic. I'm using this deck that MOTUX built, with one of the Backstabs switched for a Cheap Shot. Notice there's no Leo. An interesting choice for sure, but I can attest that the deck is still very functional. It's possible to think that Akachi is doing the heavy lifting, but they're really about even on both killing and clueing, especially since he got the Lockpicks. Once he's got the two Switchblades(2) in place of the Machetes, he'll be even more efficient since engagement won't be a concern anymore. Ever Vigilant is a great choice, too. Mulligan 100% for it if you have to.

Skids is still my favorite of the Rogues, I like him, and I have made him work on hard.

I play combat skids, with typewriter, etc. Thing is though, that what I did sounds pretty much like what you were using already. I use Typewriter, and lone wolf. Leo or Beat Cop both are acceptable. Contraband, Extra Ammunition, of course. Neck slot you will need an Elder Sign amulet. It's required. Get two. Other than that I run Prepared for the Worst to make sure Skids can find his typewriter early and often. I like to use Vicious Blow and Double-or-Nothing, giving Skids some pretty insane damage output when he commits to a combat check. Sure Gamble and Hot Streak are pretty good.

Takes a lot of XP to get, so try to pair with someone who is running Delve. Daisy is a good match.