Skip, welcome to TBN!!!!!
This discussion comes up frequently here. There is never a winner. It's too dependent on the individual operator.
In your case, being an old gear drive guy, I think you would be disappointed in HST for the tasks you listed.
You didn't mention a loader (FEL)?? Are you planning on having one?? Running an FEL is the only time I would want an HST on a 40-50HP tractor. I'm an old gear guy too.
My little JD that I mow grass with is HST. I wouldn't want it any other way.
My 47HP Ford is gear drive with mechanical shuttle. Change directions using the clutch and shuttle lever. It does not have an FEL. It's life is brush cutting and light tillage work. Although I'd like to have hydraulic shuttle, I certainly don't want HST.
My 95HP Kubota is gear drive with Hydraulic Shuttle. Change directions by simply moving a lever forward/backward on the steering column like a turn signal lever on a pickup. I have an FEL on it and use it a lot. I'm also on hilly ground with it. I like the control that this setup gives me. It's life is heavy FEL work, brush cutting and heavy tillage work. I wouldn't want it any other way.
Ask any question. Someone on here has experienced the situation and can offer their advice. Just keep in mind the uses of tractors on here are very broad ranged. All examples given will not apply to your situation.
Again, welcome to TBN Skip!!!