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Currently I am using max pressures as per the tyre placard on the Touareg and sport mode.
I have tried “comfort” but we had a fair amount of porpoising.

towing ~3.0t, 280kg
Touareg using Goodyear F1 275/45 20”
 

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If you are looking to monitor tyre pressures there are some good TPMS systems available for trailers that give Pressure and Temperature readings.
In Australia "Safety Dave" make a good system for trailer TMPS but it is a bit expensive.
I purchased an inexpensive TPMS from Amazon which seems pretty good using Bluetooth to my mobile phone. While towing you can see the temperature and pressure increase/decrease live
 

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An interesting point to note when using Valve Stem mounted TMPS sensors... these cause flexing of the valve stem.
I was removing my TPMS sensors from the caravan wheels (to change the batteries) when I noticed that the rubber valve stems were cracking when flexed.
I have since had the valve stems all replaced lest one of these decide to fail while travelling.
 
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