Don't confuse "cold pressure" with what you will see once you get going. Tires are engineered to run safely with the tire pressure changes caused by heating while driving and other variable factors.
You should inflate your tires to your desired PSI based on it before the tires warm up to operating temps instead of expecting them to be at your desired pressure after being driven. In other words...start your cold day at 95 PSI or 100 if you wish.
Personally, I would start at 95 PSI because the PSI will increase about 2 PSI for every 10*F of ambient temperature rise as you travel south. That means if you go from 30*F to 50*F those tires will be at about 99 PSI when "cold".
Going from cold to warm temps is normally not a big deal. The only exception is if your tires are at or near their max cold PSI before you start your trip. As an example, I need to run 115 PSI on my front tires and their max cold PSI is 120 PSI. If I experience a change of 30*F, I am at my max cold PSI. Any additional increase of ambient cold tire temps above that pushes them further above max.
So, if your max cold PSI is well above 95 PSI...you won't have any problem except your ride might get a bit harsher due to the higher pressure. Besides, reducing tire pressure because of these factors is pretty easy.
Don, Sandee & GSD Zeus. Guardian GSDs Gunny (7/11/15) & Thor (5/5/15)
2006 2015 DSDP 4320 4369
, FL Chassis, 2013 CR-V
2020 Jeep Overland, Blue Ox Avail, SMI AF1.