Congrats on your first MC uplander!
I only pull with the cover if it's raining. I had to do some patch work this winter on my cover (2010 X15) due to a tear from the stress of towing of the rear middle strap. Typically (depending upon year, make, model) there are 3 straps with plastic clips on the rear of the boat. One connects with the foot step in the center and the other two connect with the eye loops on each side.
Part of my problem could have been how tight I had the rear straps but I'm not sure. So, if you are going to trailer with the cover, just make sure to leave a little slack in the 3 rear straps. If you have tension it can cause a tear.
Thankfully, I called Mastercraft and they sent me several yards of replacement material so that I could do some patchwork.
The ratchet covers are awesome. But, just like everything else on our MCs, a replacement can get co$tly. So... just take care of the one you have and you won't have to buy a new one.
I say trailer without!