I guess, when you look at it, it's fairly obvious why crime fiction writers tend to base their series around the notional good guys rather than their counterparts from the underworld.
For a start, there's the expectation the forces of justice are going to prevail, at least in the long run, and that means your average criminal is going to be spending his or her share of time safely behind bars, which is hardly the sort of thing you can base a lengthy series around.
Garry Disher, on the other hand, has found a way to run a notional bad guy through a series, and while I haven’t tracked down the earliest titles in the Wyatt series I’ll have the eyes peeled for any additions.
When you’re talking about a police procedural the cop shop setting provides a set of characters to develop as the series goes on, with developing relationships, conflicting ambitions and simmering animosity in an environment that more or less equates to just add water, though when you're talking crime fiction the water's going to be something like a psychopath on the loose.
Once you've sorted out one little mystery you can come up with another sociopath, throw him or her into the same setting and you're off again. I suspect it's a bit easier coming up with mysteries that need to be solved than it is to invent crimes that can be successfully committed with the protagonist getting away in the end.
Having run across Garry Disher's The Wyatt Butterfly and The Dragon Man in the local library, I hit The Dragon Man, coincidentally the first title in the Challis and Destry novels first, and it definitely seems like a series that's worth following.
I spotted Blood Moon on the shelves at the library shortly thereafter, and a glance at the blurb on the back suggested Inspector Challis and officer in charge at the local station Sergeant Ellen Destry end up getting it on together. You can see that as a logical development of one of the subplots from The Dragon Man as Destry's marriage is subjected to the strains of personal differences, professional ambition and (I'm guessing here) teenage daughters going through a difficult phase.
Those considerations suggest it might be best to read the series in sequence.
Wyatt:
Kickback (1991)
Paydirt (1992)
Deathdeal (1993)
Crosskill (1994)
Port Vila Blues (1995)
The Fallout (1997)
Wyatt (2010)
The Wyatt Butterfly (2010 omnibus Port Vila Blues and The Fallout)
Challis and Destry:
The Dragon Man (1999)
Kittyhawk Down (2003)
Snapshot (2005)
Chain of Evidence (2007)
Blood Moon (2009)
Whispering Death (2011)
General Novels for Adults:
Steal Away (1987)
The Stencil Man (1988)
The Sunken Road (1996)
Past the Headlands (2001)
Play Abandoned (2011)
Short Story Collections for Adults:
Approaches (1981)
The Difference to Me (1988)
Flamingo Gate (1991)
Straight, Bent and Barbara Vine (crime stories, 1997)
Young Adult Fiction:
Blame the Wind (1995)
Restless: Stories of Flight and Fear (1995)
The Half Dead (illustrated, 1997)
The Apostle Bird (1997)
The Divine Wind (1998)
From Your Friend, Louis Deane (2000)
Moondyne Kate (2001)
Eva’s Angel (2003)
Two-Way Cut (crime, 2004)
Children’s Fiction
The Bamboo Flute (1992)
Ratface (1993)
Ermyntrude Takes Charge (republished as Good One, Erm) (1995)
Walk Twenty, Run Twenty (1996)
Maddie Finn (2002)
Switchcat (picture book, 1994)
