Congrats on your recent achievements! You beat me to 80 Theiving! Good job!
To answer your herb run question, I'll tell you my personal experiences. When I do herb runs, I just buy a lot of seeds. Then I go to all five farming patches. If I'm still on in an hour and a half, then I'll go do another herb run. If a herb can be saved, I save it. If not, oh well. If I'm gone for an extended amount of time, such as my 8 hours of sleep (NOT!) I still do my herb run before I go to sleep so I can pick them up the next morning. Instead of thinking: My herbs might die if I'm not on, think this way: My herbs might live when I'm not on, which would give me a profit. So I'd say just plant your herbs no matter what.
20-Sep-2014 21:42:16