One thing (in addition to what others mentioned, especially tar and chip/chip seal) that always causes me to think I've got a flat or leak is seeing my speed drop on my Wahoo Bolt when the elevation or wind hasn't seemed to change. Similar to putting black tape over the Check Engine light in my car, on long rides I try to mostly ride with just the map view showing and not speed or distance data - seems to minimize imaginary rear flats/leaks or the other phantom - imaginary brake rubbings...