I started with a Kuhn GRS-21 2 basket tedder/rake, about 7ft effective width. I used it for a few years doing around 700-1200 bales/year (with a Kubota
B7100!). As my addiction to my new hobby took firmer hold I started upgrading the tools to make more efficient use of my time: First was a roll-bar rake, then a bigger tractor, then a 16ft tedder. My reasoning for the rake was primarily second cutting where windrows needed to be combined to be worth running down them with the baler. Since the rake forms the windrow in the center (with ability for a slight offset) it took 4-5 passes to rake 20ft into one windrow compared to 2 passes with the side-delivery rake (thin second cutting). The tedder/rake didn't rake as cleanly, especially with short hay, tending to leave bits of hay in the field (non-raked) and the windrows didn't pick up into the baler as cleanly (left-behind bits), whereas the side delivery rake "ropes" the hay somewhat, making it easier to pick up with the baler (which also can be a curse!). When raking 6ft tall Reeds Canary Grass, the rotary rake would occasionally ball up grass around the baskets like giant q-tip heads, requiring 20-30 minutes to cut the wrapped grass stems and clean it out. That said, it does make really nice fluffy, tall windrows that dry well, and is fantastic for turning or re-fluffing hay that had been windrowed but sin't quite dry or damp on the bottom whereas the side delivery rake seems to roll them over, with no mixing and mostly what was the bottom ends up on the bottom again (no matter where I drive down the windrow)... I still use the rotary rake for that once or twice a year and am glad I kept it. It's also easier in REALLY thick hay to be able to make small enough windrows for the baler - and easier to maneuver into corners and over windrows since it can be lifted on the 3pt. In tight fields with thick hay the side delivery tends to make some BIG piles at the ends of the rows where turnarounds are made.
As for the tedder, I sometimes have to ted 3 times over 4-5 days to get dry enough to bale. Since I have a day job, most of my haying is done evenings and weekends and time matters. The 4 basket 14ft dedicated tedder takes less than half as many passes 'round the field. Less driving over the grass helps with better raking and pick-up (not packed down in wheel ruts).
A tedder/rake combo is great for small operations, smaller fields, thick grass, difficult drying conditions and takes up less storage space, but if you're doing 30 acres, doing more than one cutting / thin cuttings, and time matters, go for a side delivery rake and dedicated tedder, or a side delivery rake and a combo tedder/rake to do the tedding which gives you more options.