Loop-Loc are designed to fit the pool with overlaps from 12" on rectangular pools to 15" on free form pools.  When obstacles are in the way that cannot be removed, the cover can be custom cut to accommodate these obstacles. 

Handrails and Ladders

Most all handrails and ladders are installed so they can be removed.  Before the deck is poured, a "boot" is put in the ground that the handrail or ladder go in.  A wedge anchor holds the rails in place.  Generally the rails will come out, however if they have been in the ground for many years and have not been removed, they may be extremely difficult if not impossible to remove without damaging the posts. 
To test your handrail or ladder, you can remove the escutcheon cups, use a 1/2" socket to loosen the bolt (about 2 full rotations is all you need), then tap the bolt with a hammer.  This will loosen the wedge.  If the ladder or handrail has some movement in it when you wiggle it from the top, it should come right out.  If it doesn't move at all, it may have gotten sand and dirt in between the boot and rail.  You can try spraying it with some penetrating oil and wait an hour to see if it has loosened up.  If not, you will need a cutout for your cover.  Some cusotmers prefer to have the cutouts even if their posts are removable just to keep the future installation simple.