One of the ways Windows manages to support multiple libc's is by being careful not to mix allocators; if a system API you call allocates on your behalf, your libc can't free it, the system API will offer a function to free it.
Windows loader is certainly available to user programs though; LoadLibrary has been around longer than many developers.
As for older Windows systems not being able to load new DLLs, they can; the format hasn't changed in a very long time. I've had experience with installing some DLLs on Windows NT 3.51 and running a modern Firefox, which is about 20 years behind the times.
MS haven't made this work arbitrarily far back, I believe they deprecated targeting Windows XP in one of the more recent toolchains, but that was purely a "not worth supporting" situation.
EDIT: mixed up talking about older & newer