I wonder how much trust and expectation plays into this generational "happiness" factor. Older homebuyers expect less from technology as compared to those born and bred with it. Since the home buying process is typically a personality intensive experience, I imagine those who've found a quality agent worthy of their trust have less difficulty. Those expecting an app or a website to replace this human function might, naturally, be disappointed.
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Perhaps it was easier for older generations not because they didn't use the internet as much, but because they had previous experience buying homes.
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