Putting on the cover from inside the boat, unrolling from the bow, having been rolled up starting at the stern, makes it easy on and off. Set up your anti pooling poles first, then unroll and install over cleats and boat as you unroll. The issue is having dock lines and fenders hanging on the boat at the same time, you may need to move them as you cover the cleat. That is a PIA, and some may have some simple suggestions. Mine would be not to hang dock lines or fenders from the cleats. Now that new premium cover has the rubber or plastic covers over the cleat slots, I have not looked at one of those, or installed one, so I do not know if they are slotted and the cleats slip through it the same or not.
One other detail. If you don't use a bilge pump, don't tie your boat to the lift!!! Because if the lift fails, it can take the boat underwater with it. Also a good reason not to remove the transom drain plug, even on the lift. Now what I would do on a lift, is unscrew the drain plug while I was standing there and let it drain, then re-install it. Obviously this won't work if there is any chance of rain getting to the boat at all, then you have to leave the drain plug out. So for all you guys that like multiple layers of protection, your protection is going to have swiss cheese openings in it! You just can't cover all the bases...but were gonna try!