Tire pressure sensors

[quattro4awd]

Note, I may have already said....don't freak out at the flashing TPMS "warning light" icon. It will be that way until learning is completed, then a message pops up on the IHU or DIM, saying "TPMS calibration complete" or something like that, then you are good!

exactly how long does one need to wait for the vehicle to figure out the sensors and perform a successful "calibration"?  (I did a couple errands about 10 miles apiece.. total driving time around 30mins).

So everything you have looks good, those are the right settings. I get the feeling...something is wrong before you even set off. When I tapped "calibrate" with new sensors, the spinny circle just stays there, no errors, then I went for a drive. 

Have you checked codes, got any? We'd want to see if any related DTC is set and that may give you a clue. You should not need to do anything, sensors don't need to be activated, and they don't need to be learned, the car does all that automagically. You can check the TPMS IDs in OrBit "Service Tab", and even edit them, I just wouldn't do that yet, as we can watch the sensor ID fields as a way to see if the system is working, if those sensors IDs do get updated properly by the car. By default they should be all 0's to start. 

I don't know what conditions you need to get through and how long, to calibrate. I think it was about 15 min driving for me. Volvo has info in various owner's sites/manuals about recalibrating, but not on the process of learning new sensors and how long that takes.

Just to check...the car has keyless operation right? Proximity key whatever we call it, keep the fob in your pocket, touch the door handle. Probably should have asked but I was pretty sure all the US S60s are going to have that, I could be wrong. That is going to be required for "auto-learning" to work for TPMS. If you don't have that, I do beleive TPMS will still work, but getting the sensors learned will need to be done manually, added via OrBit, and I think you will use a different config setting. Nobody has tried it yet to confirm but we could work through it.

I have had my hands full with some other irons in the fire the past couple weeks (including spending this past Friday afternoon re-attaching the weatherstrips on all 4 doors of the S60).
Yes the car has keyless operation and I have physically handled the wireless receiver under the cup holder (console) and also the one in the trunk (so I am confident the system is there and functional). the driving I have done has all been short hops to run errands (10-15min drive time).  I haven't  spent any significant time behind the wheel yet.  when I perform the "calibrate" procedure the hamster wheel spins for about 10 seconds and then comes back with the "failed to calibrate, try again?" popup. after coming to a stop I have been shutting off the TPMS, then turn it back on to get the "calibrate" button to become active again and then re-run the procedure. the last time I took the S60 out I only performed the "calibrate" sequence once and when it came back as "failed...." I just canceled the pop-up then just left the TPMS system "on". (again another short hop... to get gas so I could mow the yard this past weekend). 
when cross-referencing the 31362304 part number, I found a small statement for a 2016 XC60 saying that the vehicle needed to be driven for a minimum of 15-30 mins. and then the ignition key needed to be switched off for a period of 10-15mins for the system to register the TPMS sensor ID's. all my excursions so far have only been in the 10-15min range (so maybe not enough time continuously with the ignition on driving to get the sensors to register yet). I will check the service tab in OrBit to see if any TPMS IDs have shown up. as far as DTC's are concerned, there is one persistent code for the IHU but that is about it.
I hope to be able to get the S60 out for a longer duration drivetime sometime this week, hopefully that is all that is needed to get the TPMS system functional.