Well I admit that Baloo's never flown a house so far

It could work with the time travel idea.
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Or I was thinking about a seperate idea, using the 'flying house' concept. In which some lousy inventor convinces to Shere Khan that Flying Houses are the way of the future. And once they're up and running, Cape Suzzette is now vulnerable to Air Pirates.
Although I quite don't see that one work. How would Cape Suzette be vulnerable because there are flying houses?...