i heard that if you are going to do the whole instance your toon have to be across the bridge (the bridge at the start). I never tried parking the toons at the entrance and just leaving them. I took out the guys at the bridge and guys that would agro the bridge and park them there and i had no problems. So at most you will only have to move them once.
I boosted my guys in strat until lvl 60. One of my accounts only had the orginal wow on it so couldn't go to outlands. I was going to do the trail and start boosting in ramps but forgot and next thing i new i was lvl 60. At 60 i tried to boost one of my 60s in ramps, but was only getting like 2 bars per run (no rested xp).
EDIT:
Also if you are boosting your guys chance are that you have shit gear for your team. So what i did was i did the first half of outlands (like first 10 quests that gear your guys) and all the elite quests with my booster and then said good by to my booster. This will make it so that your team will have good gear before booster leaves, unless you do the AH.
What you should also do on your team is bring them back to the lvl 1 starting zone and tag a bunch of lvl 1-4 and just have them beat on your guys to get the defense up. I found this out the hard way. When i got to outlands with my druid he had a defense of like 10. When my booster left i started to attack mobs, being melee with only 10 defense, i almost died all the time.
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