Should I be concerned about the congregation I am part of for davening on Rosh Hashana and Yom Kippur? My family has a choice of locations: Both are frum communities however the community where the residents might be considered more yeshivish has no facilities for children and poor (or no) seats for my wife to come to shul. The more “modern orthodox” community has ample seating for women and groups for the kids which would make the davening for my wife much more possible and meaningful. Am I better off davening with a frumer crowd?

Although it is impossible to give a definitive decision on this question without knowing you and the synagogues more closely, I certainly see the confort of your wife and children and your wife's ability to doven as being important enough to consider dovening in a shul that might be less condusuive to the type of intention you would like. If dovenning with more kavannah makes your wife unhappy, I doubt if it will make your prayers more acceptable.