Evil Monkey,
Assuming health, dodging & aim won't be used in the jobs, 17!/5! five-skill combo's without a double skill are possible. That is somewhere between and (10x 11)^6 and (6x 17)^6 combinations, meaning well over 1000.000.000.000 combinations of five different skills. It is highly unlikely that for the majority of those combinations a job can be thought up. Note that the combinations with re-occurring skill (Hide, hide, traps, traps, traps for example) are even omitted from this calculation.
For that reason I recommend working the other direction: Think up several tens of jobs, make the skills make sense and use those things as the building blocks of your story.
For explaining what bounderies you want to stay in, you shouldn't be needing the 12 job scheme with 3 times 4 jobs which you put up earlier. It will only confuse people and keep them from seeing the key ideas. I recommend to just start discussing how many times each of the skills should be present in a set of N jobs that you want to use and why and I'll get you a group of sensible jobs in a week that can be put in any order you like and given all difficulties, luck, money, risks & XP you like (if not someone else does). If you want more flexibility, you can get a lot more jobs then you'll need and discard what doesn't fit you scheme.
Don't get me wrong Evil Monkey, the following paragraph is not intended to offend you, but to show the problem I have/see with the approach you suggest:
Right now, I'm either stupid or you've given vague discriptions of what you want and you suggest discussing abstractions of these vagueness.
However well the concepts behind your ideas might be, if the latter is the case, then I doubt discussing it will work. This firstly because you will waste a lot of effort on communicating what are the ideas behind the vagueness. On top of that, vagueness leaves to much room for people fitting vagueness in their own schemes, while the realistic counterparts might not fit everyone's mental concept in the end.
PS.
I trust you can add a sensible set of difficulties, luck, XP, wage & risk to any set of jobs that people might give to you. Really! Just give it a shot