My main tip would to be to listen to your skin. I still end up in the same trap every year when the seasons are transitioning and it's getting a bit colder, during that time, like most people, my skin goes a bit off.
Adding tretinoin on top of that is a recipe for disaster, my skin's barrier is melted off and is extremely sensitive. If your skin is at all a little bit sensitized, I would recommend skipping tretinoin.
Of course, you have to build up tolerance but I believe that destroying your skin barrier is a bigger set back than taking a longer time to build up the tolerance to use tretinoin everyday. Also maybe protect sensitive areas like the corners around your nostrils as those areas are particularly dry for me.