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Yes you can but be sure to water them in with some super thrive and root stimulator in the water. Spring is truly always best but it can be done this late in your area. Be very sure to keep a close eye on the soils moisture over the winter months. Here is an article for you to check out on this too:

https://www.gardeningknowhow.com/ornamental/flowers/roses/roses-winter-care.htm

https://www.gardeningknowhow.com/ornamental/flowers/roses/how-to-transplant-roses-tips-for-transplanting-a-rose-bush.htm

The tiny holes are likely caused by some small beetles that poke holes in the leaves to such out juices for their survival. Spraying the roses with a good insecticide should take care of the problem, use the least harsh insecticide first, like a Safer brand and move up if need be. The holes will not disappear but should stop being present.

You can certainly do this, however the owner will sacrifice many blooms by doing so. If pruning them back to the same height is only a light pruning on most of them, then it will probably work out okay. Just be sure to let them know about the blooms reduction if they are pruned back heavily.

Knockouts are hardy rosebushes and will usually come back well each year. You will likely need to prune out some of the dead canes each spring but otherwise they should do fine. Be sure to wait for the bushes to start to leaf out before pruning what you think is dead as sometimes it is not.

I do not personally know if the Knockout line of roses is available in your area, if not, you might try looking for the Homerun family of roses, or one named Winnipeg Parks for a rosebush that is very similar to the Knockout but said to be a better bush by some. Here is a link to a company in Canada that should be able to help you: https://palatineroses.com/

There are a few reasons why any rosebush may not bloom well or at all. We need to be sure their root zone is happy in their new home and 9 times out of 10 the top part will follow along happily. Here is a link to an article that should be helpful to you: https://www.gardeningknowhow.com/ornamental/flowers/roses/no-blooms-on-roses.htm