Using a pick

I usually paint solo. Sometimes I hire a helper for a day or two here and there. I did alot of exterior painting on brick rowhomes this year. I'm only painting the windows, doors, trim and cornices. I've been doing all this work off of ladders. I've been wondering how much faster that I could paint if I was on a pick. The main issue is to set up a pick I need to have a helper, but I right now I'm basically a one man show. So I don't know if it would be worth the trouble of having a regular employee just because I can't physically set up a pick by myself. I'm trying to figure out if painting from a pick as opposed to a ladder with a standoff how much more time am I going to save ?

Also any recommendations for using a pick 3 stories up would be good too.