I bought the Pressure Pro several years ago. At the time, there were fewer choices. I had trouble getting it set up at first. After that, it has worked well for five or six years. I think the batteries are likely to die soon. Then I will need to decide if I want to buy all new sensors or an all new system. Apparently, Pressure Pro will sell new sensors as replacements for $35. So, it will be $350 vs $500 for something like the TST.
One reason to change is that the Pressure Pro I have does not look very nice on a Beaver dash. Maybe the new ones look nicer.
At about the two year mark, I had an unusual failure. While parked, one of the sensors got hot enough for the plastic to get soft. With a 100 pounds of air pressure behind it a pinhole formed and slowly let all the air out. I think the battery shorted. Pressure Pro said they had never seen anything like it and that I had it too close to a source of heat. They sent me a free replacement.
One thing to consider with these systems is that their sensors become the only thing that keeps the air in the tire. Normally, there is BOTH a valve in the stem and a cap that screws on as a backup. These systems depress the valve stem and effectively disable it. The sensor replaces the cap. So if the sensor is damaged, the air can leak out. The caps on my tires were metal. The PP sensors are plastic and a much larger target for road debris.