Craig,
I have Racor filters, but they are pretty similar to Dahl. I only drain the bowl if there is gunk in it. On my boats that has never happened, but I have a small tank on the sailboat, so my fuel is always fresh. The powerboat's fuel system is only two years old (new everything two years ago), so it hasn't had time to gunk up yet. I also go through about two tanks of fuel a year, so the fuel is never old.
The hand pump should pull fuel through the lift pump. If it didn't it wouldn't be of much use.