I found a rollabar or single line wheel rake makes a better windrow for square baling while v-rake without kicker wheel, makes a better windrow for a round baler.
A v-rake, set up properly, makes two windrows lying side-by-side like two Twinkies in the package. This causes more hay to be feed into the outside edges of the big round bale so you don't have to weave back and forth to get a well formed bale. But this makes it tougher to feed a small square baler to get nice, even flakes.
But, it all depends on the operator raking. I tell my guys to just do down-and-back trips. picking up the wheels when turning around, then come back and do two trips around the outside to clean up the ends. I can then bale the two outside windrows first, then do down-and-backs myself.
I've found that turning a v-rake with the wheels down makes for sloppy windrows in the corners AND, more importantly, tears up the tines on the rake with the stress on the wheel!
I have not found any difference in drying between rake types. A v-rake will make a bigger windrow than a rollabar which means that wet hay will stay wet longer, but it does dry.
Hope this helps.
Ralph