How I see it, the marriages of Josiah/Lauren, Joy/Austin, Joe/Kendra, and Josh/Anna were probably arranged (or brokered) between the families. Maybe some of the boys were presented with a short list of “available girls” and had the freedom to pick one, but I think that’s about as long as the leashes got.
I think Ben and Derick independently approached Boob because they thought one of his daughters would be good for a wife, and once they had his approval, they were paired off with whichever daughter liked them best. I don’t think it was an arrangement between families, but I do think those relationships were more or less brokered by Boob.
I think JD/Abbie and Jinger/Jeremy were love matches. Both couples have the kind of chemistry that makes me think they just fell for each other. That’s not to say I think they have great relationships (I don’t), but they seem organic.
I think Boob doesn’t arrange anything for Jana because she hasn’t especially liked any of the men who have come calling and she’s too obedient and useful for him to want to push her into a (punishment/prison) marriage against her will.