I probably need to post this on some GIS discussion board… if you had 2 years time and a few $1000 to spend, what would be the smartest use of time and money to turn yourself into a GIS guru ? What software should you learn to use or buy, what training should you invest in ? What will be the trends over the next few years or so ?
UPDATE
I have gotten 2 pretty good responses to my post on thegisforum.com.
Adventures in Python, Petroleum Data & GIS 
Okay, I did post something similar on giscafe.com and thegisforum.com – let’s see what I turn up with from those communities.