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A hobbit's weakness would not lie in their being "evil" or "good." Rather, I was speaking more to their inherent mortality and the world-view within Middle Earth that hobbits were inherently "weak" when compared to Elves, the Noldor of old, some Men, etc. They were mortal, prone to illness and death, not as spiritually aware as the Elves. Much like most in the race of Men. In that sense, I said they are "weak." They were taken for granted, in other words. True, it was also their inherent earthiness and simplicity that makes them so attractive at the same time. Gandalf loved the "halflings" because he too was an exercise in humility, being one of the greatest Maiar, but taking upon himself an inherent humility upon his venturing in Middle Earth as a wizard. He, I think, prophetically recognized their greatness though he did not understand why or how they would play such an important role at the end of the Third Age. Hence the beauty of the whole Story which brings us out of the mythic stories of power, magic and struggle to a more "earthy" reality that we are all familiar with. I think all this goes to show that the mighty throughout the ages could not accomplish what the "weak and foolish" did at the end of the Third Age; though without the help, inspiration and wisdom of the great elves and men of ages past, even the hobbits probably would not have succeeded. And herein lies the wisdom of Eru.
As to questions of good and evil, I think the hobbits could just be as prone to evil and pride as anyone else...perhaps they had just not had the opportunity, as other races had, to exercise it in any kind of terrible way. Bilbo and his Ring. Gollum and his Ring. FRODO and his Ring. They were all ensnared, to some measure, by the Ring. The Ring brought out the worst in everyone, including hobbits. Only a few wise were able to resist it's power, though no one present was strong enough to actually wield it in Middle Earth in the Third Age (minus Sauron.)
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