Replace TPMS sensors with new tires and move old set to winter tires?

I'd just stay the course: replace the tires on the stock rims, don't touch the TPMS sensors.

 

Second gen owners with 06~07 model year are just now starting to have failing TPMS, so maybe you're ok for the lifespan of your next set of tires.

Plus I guess I'm just expressing my opinion: I wouldn't worry about them till they've failed and some authority is forcing me to do something.

 

Mine lasted 9.5-yrs and 150,000 miles.
You need to tell us your miles on the ODO.
The TPMS turns itself off when the car is not in use, so the more miles you put on per year, the less life you will have left in the batteries.

 

If it was up to me I would not replace them at all. They aren't really accurate. I think they only alert you when you've lost at least 5 lbs of air. And then they don't tell you which tire is low. You can tell that by looking or checking your air pressure with a gauge at the same time you check your oil.

 

My 2006 had one sensor fail. When I replaced 2 other tires, I replaced 2 more sensors. There's still one original still working after 9.5 years.

My wife's CT200h had the TPMS warning light come on. All the tires looked fine, but one of them turned out to have about 20 psi due to a small nail. The warning light did its job by identifying a problem before anything dangerous happened.

 

I think it's mostly time. I had one failing in rav4 that is little used, under 50,000 miles, at the 8 year mark.

 

Pearl's sensors are still working (2007). At any rate, I don't think the sensors will fit in the steel wheels. They are designed for a thicker rim (they are part of the fill valve). If you do try, get new "O" rings for them. Those loose their pliability and may not seal after moving them.