TPMS on 19.5"

The stock ones only work up to 95psi. After that they error. If I had it to do over again I would not add them to the 19.5" setup. They don't really serve a purpose if the dash light always says there is a problem.

I have a stock TPMS system on one of my vehicles and an after market system on my RV with 19.5's. The TPMS only measures air pressure not tire size. You will have a minimum pressure setting built into your factory TPMS. As long as you keep your pressures above that pre set minimum you should not have an alarm reaction.

I bought a Superchip programmer for a Dodge and it has the TPMS module reader built in and I am able to adjust my tire pressure minimums with the Superchip as well.

I would say no. A stock Ram 3500 will have load E rated tires, so that is what your stock monitor is set for. A load E rated tire will be rated up to 80 psi. (at least on my Dodge/Ram with Cummins, the truck's sticker was 60 psi on the front, 70 psi on the rear. , I haven't double checked inflation charts recently but I believe 80 psi is the low end and 110 psi is the high end for 19.5's.

I've got 19.5's but don't have TPMS monitoring so this is just an opinion.