This is like starting trucking all over on my first day!

Lol see what i mean, take ur time and think it thru. Once u get in a habit u wont have to think about it. Although i still catch myself every once in a. Blue moon forget to feed strap thru rub rail

 

I hope you just pulled the straps off the winches and put them behind rubrail then back onto the winches...

 

Put a bump stop between the frame and axle on that axle or move the winch rearward one winch length and maybe add 1 more forward at that same distance from the center of that axle

 

Yes. Even with sliding winches they can slide back above the tire. Have to put a bungee on the unused winch so it doesn't slide back or they put a bolt in the winch to track so it doesn't slide back that far.
Sometimes trailers take along time to fully inflate the airbags. If they leak, or the bags dump when the brakes are set it could take some time to air them back up.

That's usually when it happens, when the airbags are low. But not always. Might want to remove the winch and use a ratchet strap? They make them for 4" straps. Although you can't tighten them down as tight.

 

Grab a couple stake pocket winches for that area.

 

yeah, i second the stake pocket winches. they even make 'backwards" ones for connies.

way way way better than hand ratchets. (if you can make it work, not always possible, right tool for the job and all)

 

Do stake pocket winches work on a Conestoga?