Lets talk about how to powerlevel for a bit. Some skills are easy to powerlevel, others take a bit of work.
At the start, even as a peasant, Powerleveling ambush by just sneaking in someones home is relatively easy. Bogeys cant get you, and you soon get enough skill that the townsfolk start to take notice.
The second thing to powerlevel would probably be knapper/thrower. Easy to do with a macro. If you can manage to convince a peasant to come with you, then all the better.
Powerleveling swimming can be tough if your not already a novice in swimming. If not a novice, you need to take a risk and find an area of river that is not at 7/7, and you need to worry about fish. If you are a novice, just find an empty murky pool with a follower and train up to legend.
Powerlevel armor user, shield user, fighter, and dodger. This is simple, but you need at least a shield, and some copper armor head to toe. (If you want to gain in armor user). Then just look for a critter, like a duck or groundhog. Get in close, grab it with wrestling, then sit on the ground and pass time, taking hits. You will be legend in no time.
Powerlevel wrestling by using a macro.
Powerleveling weapon skills generally means fighting bogeys. Highly recommend getting full armor and powerleveling defense first.
Powerleveling observer I don't know.
Anything to add, feel free.