Weird Monarch Illness

What is the source of the caterpillars you’re raising? Are you collecting them outside? And are you keeping them in a cage that keeps other insects out, even tiny ones? My first suspicion here would be some sort of parasite. I have seen chrysalises die or caterpillars fail to form a chrysalis when they were infected with tachinid fly larvae. If the chrysalises are oozing liquid from tiny holes, it might also be a braconid wasp problem. I haven’t observed those yet but based on the pictures I can find they are tiny. It looks like you’re using one of those “Kritter Keepers” or whatever they call them, which have lids that would allow those insects to get in. You might want to try pulling pantyhose over the lids to keep them out if that’s the case. If you can rule out parasitoids, the next possible explanation may be some kind of pathogen such as a bacterial or viral infection.