Gears vs HST is always a hot topic and never really settled, in looking on lots and talking to sales people, you will find in the size you are shopping HST is the preferred choice by a large margin. I know many who grew up on geared tractors and really didn't think the HST was that big of a deal. We have tractors from 22 to 85 HP, crash box, synchro-shuttle, hydraulic-shuttle and in that size, I won't consider gears. A few years ago a friend bought his ideal retirement tractor with a synchro-shuttle. After using my HST quite a bit, he wishes he had gone HST. He really likes our hydraulic-shuttle also in the larger machines, it is just not available in many of the tractors of the size you are shopping.
For many of us, age has pushed us away from geared units as foot clutching really gets tiresome as father time catches up.
When looking at cutters, consider your uses and weight of the cutter. I use a 6' LP that weighs 1100 pounds with my L5740HSTC and the front end gets really light on anything other than flat ground, many including me find mowing without a FEL is smoother and gives much better visibility.