My FLHR is my first tubless tire motorcycle.
Habit has me checking the pressure regularly.
I've been pleased about the fact that I rarely have to add air to keep the tires at proper pressure.
My spoke/tubed tires in the past needed very regular air to keep pressure proper.

Is it just my imagination or do tubless tires like those on my RK have less need for air fill-ups?

 

Having had both types, the tubless do seem to require less fill-ups that the spoked wheels. Why? I have no idea.