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Yes the flange size is super important.
I confess that when DD was born and I was in hospy trying to hurry up my milk, the MW said pump on the lowest setting for no more than 10 minutes and of course in eager / desperate new mother mode I pumped on a high setting for 20 minutes and the next day my aereolas were purple with bruising :(
When I was expressing regularly at the start, I used a Medela Symphony (rented it from the chemist) and it was great. Since then I just use an electric Medela pump when I need to and it hurts a lot :( Perhaps a pump upgrade could help the pain during expressing, especially considering you are doing it so frequently? Sorry, no advice on the refilling pain - I just hope it improves for you.