Is it possible to have all 4 max out at the same time?
I'm always taking the option that gives the most rep even with the downside, because over time, that extra rep and the extra token should get you finished sooner. My guess is to just use some of the tokens on the group you insulted.
if you're worried about the negative reputation hits and getting all 4 reps to full the TLDR is as long as you pick a faction for the week that gives you the 4th token, you will never actually lose rep with any faction, since the weekly quest offered by the token gives you 100 rep and you can use multiple tokens on the same faction each week.
The rep rewards don't seem that good
Venthyr did it better.