I did this a few years ago on electric. I think the key is to not play the old guitars before selling them. We get in a headspace of wanting to clean house, but then we decide we need one more spin around the block before selling the old guard off... that's where we mess up. Once you decide you want to sell something, take pictures, box it up, and have it ready to ship once a buyer pulls a trigger.
Sold all my electrics, and then bought my Les Paul. Then I did a similar thing with acoustics. I bought my J-45, then gave my old seagull to a co-workers' son and I traded my Martin to Steve at vintageparlorguitar.com to cover the cost having my grandmother's guitar reworked. Despite owning two acoustics, the Gibson is the only one that ever gets played, and my grandmother's guitar hangs around for sentiment and the occasional recording where I need that small body sound.
I think at this point, I would probably be fine selling all my electric stuff and my J-45, giving my grandmother's guitar to my brother (in the hopes one of his kids play some day), and picking up one really nice instrument. That Bourgeois I played recently really did rock my world.
Going real simple and just having 1 guitar that doesn't "have" to be plugged in sounds really freaking nice right about now.
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