I used to hand express alot. 3 x a day when I was in work and at least once a day to build a freezer stash.
I use avent bottles as I found them to have wider tops than some other brands.
Once your milk lets down if you've got the bottle positioned well you don't really have to look at what you're doing. I used to watch tv whilst I expressed in the evenings.
I always get more milk in less time by hand expressing than using pumps.
If you are looking at increasing your supply though I would move the expressing to every 2 hours during the day and 3 hours at night - making sure you're expressing at least once between 1am and 4am.