Hi alien,
Hope you're still around to see this as you posted it a while ago.
Although it doesn't specifically mention Steelworxx or the Looker range,
PansyTart's measuring system for custom-fit devices, pinned to the main Mall forum is a good starting point for the hows and whys of measuring up for a custom device.
Also, there's nothing like you're own experience for finding out what does and doesn't work for you, so if you don't have one already, maybe get a relatively cheap device like a CB6000/6000s (or similar eBay-sourced knock-off) and try out the different ring sizes, spacers and - if you can go the extra expense - cage lengths. You can then translate these dimensions to a custom device, with a little tweaking.
That's basically what I did (along with a fair amount of wrapping string round my bits and measuring the results!), and my Looker 01 arrived last week. I posted a fair bit of detail about my measuring process and ordering experience
here, but am looking (ha!) to start a new thread in this sub-forum about my experiences, as these sort of questions come up a lot. Obviously a custom device is a significant investment for most of us.
I'm easing myself into the wearing of the Looker (a rigid metal device with a fixed urethral insert isn't the kind of thing you can rush into long-term wear with!), so haven't had it on for extended periods yet, but I've very pleased with how it's turned out.
However, I agree that Steelworxx's site can be a little confusing regarding sizing, and I only got the correct guidance when I contacted Dietmar (the owner/engineer) directly - to cut to the chase: yes, the overall length of a Looker should be pretty short, shorter, in fact, that your measured flaccid length.
Cienna