I think that Ranger increases chance to find other players, and I think Izual said this in the Questions and Answers: that 150% Outdoorsman is very good, and 200% outdoorsman is just about perfect. 100% is about average I think then.
For healing cripples, I think that 100% is pretty good for Doctor skill. Maybe more for a 95% chance of it working. I think that Luck (SPECIAL) contributed to it as well. Also, you can heal anything with a really low Doctor skill, but your chance of doing so are very low, but it isn't that you need a certain skill point to be able to do it.