The Airflex extensions on our 2012 had a similar problem. The inner stem - which depresses the stem of the tire valve - was too short. My solution was to cut off a small (1/8 to 1/4 inch) of the threaded section to expose the inner stem enough that normal pressure gauges and fill chucks will work. Others on the forum have had the same problem and several have used the same solution. I believe some have found pressure gauges and fill chucks with longer stems which work without modifying the Airflex.
By the way, my issue was with the outer duals. The outers on our 2012 Solera have a pressurized right angle extension on the valve (to point the air inlet in the right direction) followed by the Airflex to get the fill location beyond the wheel cover. I suspect the "dual extension" on these caused a build up of tolerances - and hence the problem. Also, with all that weight on the rubber valve stems, I have used wire ties to both secure the wheel covers to the wheels and to secure the extensions to the wheel covers. Otherwise, seems these extensions would whip around a lot at speed. Not recommended by Airflex - however Airflex says use metal valve stems, I believe...
2012 Solera "S"
Calif SF Bay Area