The shire is a confusing place where the logic makes no sense bc most of its lore was established before tolkien knew his satire of modern rural english polite society would be going into his fairy tale.

In lotr he tries to salvage it a bit with the chapters showing the shire outside of hobbiton, and the whole very clearly premodern social systems, but that just makes the rural victorian aesthetics (rsvp letters! umbrellas!) stand out more and beg for explanation.

We don't see them doing so in books, but to live like that someone must have laboured for them. Also kulaks were diverse groups, there were small time tyrants making life miserable for few agri labourers and there were landlords who did nothing except buying land and collecting rent (and all between). Not to mention books, especially adventure ones do seem to skim on mundane everyday lives of characters.