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I have always suspected that the Shire did have a monetary system - the appearance of silver pennies in Bree being evidence of this.
The Bagginses were apparently "well off" even before Bilbo's adventure. Bilbo appears to have led quite a comfortable life, at any rate. So I imagine that, even were it not for the dragon-gold, Frodo would have inherited enough money to live on.
I think, though, that the treasure of Smaug might not be all that hard to convert into useable sums of money. It was not all "little arkenstones" - in fact, it seems to have been, for the most part, gold. I don't doubt that gold had great value in the shire, nor that there were hobbits wealthy enough to buy it. Gold ingots could always be melted down and sold to a number of buyers. Gold coins could probably be used in transactions among the very wealthy (the Tooks or the Brandybucks, for instance) or could perhaps be exchanged for silver at Michel Delving. Gems could probably be sold to wealthy hobbits (Tooks and Brandybucks come to mind again).
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