Hi after a couple years I've decided to give the main quest another bash and finally try to complete (again!), I'd figured I'd kill two birds with one stone and do it with Julan/Jasmine I've already picked Jasmine up but I wanted to do some adventuring and bandit slaying before meeting Julan because I don't want to go get straight on level one and have to kill those Clannfears. So my point is what relatively easy caves or quests can you recommend just to get my character feeling a little more familiar with Vvardenfel before going on to save the day.

Addamasartus is a good one to start and then go to balmora and do either fighters or mages or thieves guild quests, whichever suits your build.

They have easy quests as the developers expected you'd land here first after Seyda Neen (even though you don't have to).

Also there are pretty easy caves along the seyda neen - pelagaid - balmora road too.