Nice looking doors. My wife wacked a door on her horse barn. She bent a rail, so off came a door (two piece rail). In this case, the siding is metal (about all you see around here), so changing out a warped 2 x 6 was easy, as was rail removal/straighten/reinstall).
I have found that the metal flashing cover on the horse barn doesn't hang down far enough. Particularly tough on the prevailing wind side (snow in winter, thunder storms in summer). The flashing on my shop (similar construction, better outfit: Lester buildings) is much better, hangs lower. Adjustment of the trolleys is then done on the inside.
I have used a couple of things to make the horse barn better (I should probably call the local Lester people and see if the flashing is the secret, or something else detail wise). But nothing has made it perfect. I added a piece of flashing to the door face to stick under the rail flashing. Better, but snow still gets in. Then I installed a side strip for a roll up door on the bottom of the header (conventional house/garage door side strip). Better, not perfect, but rain is not an issue any longer (at least not enough that I remember any issues from last summer).
I like the look of the wood siding, but it is a lot more work to maintain. Nice job!