My leuc has grown only one small-ish pitcher so far this year, but did bloom. Your leuc looks reasonably healthy but the other Sarr doesn't and not only because it's floppy. It looks a little withered and the color seems a little off, kind of like a person who is sick. If that were my plant, I'd pop it out of its pot to have a look at the condition of the roots. And by "pop" I mean gently slide out the potting mix + root mass with minimal disturbance.
FWIW, I grow my Sarrs outdoors year-round in hardiness zone 6A-B CT and they freeze solid every winter, but I prepare them for it. I dig up a small area, just deep enough so that the rim of the tallest pot is 1"+ above ground level and then I put all the pots in there, putting some dirt back beneath the lower pots so they also extend above ground level. Then I fill in around the pots to avoid leaving any empty space between them but without dirt spilling into the pots. Then I pile fallen leaves, pulled weeds, and twigs over them, aiming for a foot or so. That setup offers protection from the coldest cold (they've survived -10F) and it also buffers them from repeated freeze-thaw cycles, which might be equally damaging. I slowly uncover them in spring.
Depending on where you are, it looks like you could be a full zone colder than me, so YMMV. I think it's easier and more reliable, when possible, to adjust natural conditions as needed than to try to provide a suitable but completely artificial conditions.
A couple additional thoughts about over-wintering not-quite hardy plants under leaves in case you might be interested: First leaves are not all alike. Red oak leaves are awesome, curling up a little when dry and insulate like down in a sleeping bag without restricting aeration. Maple leaves are inclined to mat down into a soggy mass and can suffocate what's underneath. I lost my easy supply of oak leaves so I use a mix of less ideal leaves now, which is why I've begun adding twigs and weedy grasses to provide some structure.
Another thing learned from unfortunate experience is that snow can be an enemy, not always a friendly blanket providing additional insulation. Back when we tended to get a more persistent snow cover here, it dawned on me during an especially snowy winter that water from snow melting at the top on a warm day has to be percolating down and might re-freeze below. A little excavating found a couple inch thick solid mass of ice and leaves on top of everything. That was the only time I lost previously healthy CPs and hardy orchids during the winter. I started erecting a lean-to after that to keep most of the snow off. I keep far fewer plants now so don't do the lean-to anymore and instead just use my snow shovel to slice the top off of our increasingly rare snow accumulations.
