I had a Case 430 and 530. Both fine tractors. I hadn't considered the HST because I know nothing about them. I've never even driven a tractor with shuttle shift. Everything I've been around has gear and clutch.
I suggest that you stop by a dealer and try out a tractor with shuttle shift. HST has a lot of advantages, but also some disadvantages. I've said this many times, but I would part with the MX6000 (HST) long before the M6060 (gear drive with hydraulic shuttle).
In my world, the biggest advantage of HST over gear drive is that engine RPM and ground speed, or more specifically, PTO rpm and ground speed are not directly related which is not the case for gear drive tractors. This is a very convenient feature, and many of the bigger tractors such as the M7 offer this via a CVT. But as with many things, it takes more thought and practice to operate a gear drive tractor well, but neither is required for HST.
I've been watching a YouTube channel for the past five years or so that features a small cattle farm in upstate NY. He has five or six IH tractors, most don't have 4WD and none are HST. He uses them all in just about every way imaginable whether it's moving hay bales, loader work with a bucket, cutting hay, tedding, raking, baling, pulling a disc, pulling trailers, and so on. I think he'd laugh at the notion that 4WD and HST are essential features, but he's not on a very hilly property, and the biggest hill that he has only sees a tractor in decent conditions.
For me, 4WD is essential, but HST is not.