I do the same thing! I have 3 TTs all at different levels and a very good CDP. I get hooked on one of them and listen for weeks. Then for whatever reason I will switch and repeat.
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I have an old T-Bird with a Pioneer cassette deck. I use it all the time. I miss the days of making tapes just for car. I don't think your nutz, I think it's awesome. I need to source a good replacement deck as the Pioneer is in needs of belts.
I remember having a good Jensen unit then a good Blaupunkt. Off to the bay to search. =)
I own two entirely separate systems fed by a total of five turntables, each with a different tonearm and cartridge. So I binge on listening to one system with one turntable/tonearm/cartridge for weeks on end, and then on another. But it's all vinyl almost all the time. In one system, I have an Ayre C5Xe-mp, which is one of the best one-box cdps I know about, and on rare occasion, like when I want to read a book or when we are having a party, the Ayre takes over from vinyl.
What? No pics of the Walkman? That's halarious!
I used to do the two system thing, but then got frustrated as they were on different floors in the house and what floor to keep the music on became the issue. My solution was to simplify, and boy did I. Now listening to a vintage Sansui system not far from what I started with 40 years ago. Go figure huh?