There is a guide to the jobs. Forum/guide/guide to the jobs of pimd It tells all you most of the things need to know.
2-2-2-2-1 or 2-1-2 depending how much energy you are loosing, you will be able to tell quikly if you know your regen
It's best to farm or party, though, instead of doing very difficult jobs. You'll fail those jobs enough times for them to be a not very efficient way of earning money.
Best is to unload on jobs before sleep or when busy...hit parties with pattern jobs may fail many times
I completed jobs a few months ago i always just unloaded. Word to the wise though, the more higher tier ppl you put in, the easier the jobs get.
I hit any job 3-3-3 with no fails and it gives me the perfect regen, just like prank is 3-3-3. I'm not sure what it will be if you fail one of the hits, though.
Depends on your tiers / stats because if you are just 50-100k stats going for the plank job then you'll lose more than 3% health