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Originally Posted by Rikae
Yes, but it isn't necessarily a compliment.
"I don't know half of you half as well as well as I should like" implies that he would like to know half of them better, but also that he wouldn't like to know the other half better - perhaps he feels he knows them too well already!
Likewise:
"I like less than half of you half as well as you deserve"
on one hand means the "less than half" deserve to be liked better than he likes them, but also means "more than half" don't - he likes them exactly as much, or more, than they deserve!
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Well he's actually addressing the people who he directly mentions in the statement, the people who he hasn't taken the time to get to know as well as he would have liked, and the people who he feels he has not esteemed enough. These are parting words, and he is trying to make amends with those who have not been his best friends, but in such a way that he is not delivering mere platitudes which can easily be forgotten.
Nobody would forget
these words on the other hand!
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Originally Posted by Damrod
My impression was that the meaning of it was up to the hobbits. A "glass half full/empty" thing. The S-B's would take it differently than say, the Proudfoots (feet?). Or, it might be some kind of grammatical English-professor inside joke of Tolkien's.
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Yes it is a glass half full/empty statement, and understanding it as a compliment would indeed depend upon the listener being well-disposed towards Bilbo, as it would be very easy to take his words as an insult! But logically borken down, they are a compliment.
He's also, in the words he
does not say in the second clause, being slyly self-complimentary, saying that in fact he
did take pains to see the best in most of the Hobbits he knew. But that would be inference and inferring things is possibly the biggest joke of all in his statement.
