Tomato skin in roasted tomato soup?
I wouldn't bother keeping the skins, if they're hurting the texture.  Many recipes using tomatoes end up removing skins for this reason. My exec chef showed me an easy way to remove the skin from tomatoes (we were doing tomato concasse):  


Wash tomatoes thoroughly, and slice a shallow cross in the bottom.
Bring a pot of water to a rolling boil, and also prepare an ice water bath nearby.
Drop tomatoes into the boiling water for 30 seconds to a minute, until the skin starts to crack.
Using a slotted spoon, transfer tomatoes to ice water to cool for a minute or two
Peel -- the skin should already be peeling back around the X-mark.