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Knock outs are very hardy but it is important that they go into dormancy well-watered. A dry plant is susceptible to winter die-back. Stop fertilizing and don't prune in the fall. When the ground is frozen, put 4 inches of mulch over the crown (and remove in early spring). The idea of winter mulch is not to keep the roots/crown warm. It is to minimize freeze and thaw cycles. That's it!

I usually do a thinning pruning on mine once the cold temps and frosts have sent them towards going dormant for their winters nap. You could also prune them down some in height at this time too if so desired. Then come spring, I wait for them to start pushing out their leaf buds and prune out the dead canes or broken canes and do a shaping pruning.

In part, the answer depends on what type of holly you have. A few like very moist, if not wet, soil - not rose friendly. Many varieties of holly sucker and may encroach on the roses if these aren't promptly removed. Place the holly where they won't shade the roses unless you are in the south where 2-3 hours of late afternoon shade won't harm the roses. Space the plants so there is ample room for the mature size of both plants otherwise they will compete for nutrients and a crowded rose will be more susceptible to foliar disease without good air circulation.

Knockout roses are roses are Rosa radrazz. These articles should answer all your other rose questions
https://www.gardeningknowhow.com/ornamental/flowers/knockout-roses/

Books are written on how to prune roses but Knock-Outs are easy. Anytime you notice dead or diseased wood, prune it out right away. Other pruning is done in early spring just before the leafs come out. You'll notice buds along the canes starting to swell: this is pruning time. Don't wait until later because the plant pours lots of energy into leafing out which it loses if you subsequently prune leaves off. And, it is easier to see the internal structure and what needs to be pruned. It used to be said prune when forsythia blooms but I find that timing too late by 1-2 weeks. First, remove old canes to the ground; more flowers come from younger wood. Remove branches that cross and rub against each other and dead, diseased or damaged canes. Remove canes which grow toward the center of the plant; opening up the center helps increase sunlight and improves air circulation. This helps prevent disease. Read this webpage: https://www.gardeningknowhow.com/.../knockout-roses/prune-knockout- roses.htm

Have you had some real cold evenings in your area? Sometimes the cold evenings will shock them into going dormant for their winters nap. Here is a link to an article I wrote on this subject that should be helpful to you as well: https://www.gardeningknowhow.com/ornamental/flowers/roses/yellowing-rose-leaves.htm

And this one as well: https://www.gardeningknowhow.com/ornamental/flowers/roses/leaves-falling-off-roses.htm