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The articles of confederation actually weren't a total disaster. The confederation passed the Northwest Ordinance, which set in motion the process by which much of what we now call the Midwest became states, plus it prohibited slavery there. It might have been nice to have similar treatment of land acquired in the Louisiana Purchase, but I don't think Pres Jefferson was temperamentally inclined to any such thing, especially given that the Purchase was a stretch of his constitutional authority as it is (or at least so he thought).
The war of 1812 always struck me as sort of pointless. No one ended up with much to show for it afterwards. Although it's fun nowadays to visit Fort Henry in Eastern Ontario, get the kids to dress up in redcoats and listen to the guide tell them to scream at the Americans across the St Lawrence.
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