[littlemanpoet]

Originally Posted by the guy who be short

When you write, you write what you feel. It's notable that all of Tolkien's absolute leaders - Sauron, Morgoth, Saruman - fell on the side of evil.

Fair enough; we can obviously discuss political rule as LotR bears applicability to our own experience. We really can say no more regarding Tolkien's personal views than that.

Tolkien's positive monarchies and leaderships - From Elessar down to the Thain of the Tooks - assumed the form of benevolent dictators respecting individualism.

I realize that you're using an umbrella term by calling all of them benevolent dictators, but it's a mis-construction, my dear guy who no longer be so short. You lead into the differences later in your post. There are two types in the Shire: Sam as Mayor, and Pippin and Merry as hereditary earls. But hereditary earls are not dictators; they were answerable to their overlords, and also answerable to their Councils or Things (Nordic word for council).

This is evident in the Mayorship of the Shire - a leader with no actual duties.

It should be understood that there are two types of leadership responsibilities: those of Head of State, and those of Policy Decision-maker. As with the current British royalty, the Mayorship of the Shire is head of state; that is, figure-head, responsibility lying exclusively in the realm of ceremony.

Likewise, the Thain of the Tooks and the Master of Buckland exerted no real authority.

Not so. They exerted the authority of head of their respective families. Whereas this authority did not carry beyond their extended families per sé, the respect for them held by those not directly related, translated into the authority of reputation, a powerful thing in itself in more loosely governed communities such as the Shire.