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I like the idea in theory, I've done something like this with extended family before. Something like this requires a high degree of trust if any important accounts are involved. But yeah it's doable among people who know each other and trust each other. However, I will say that every time I've tried to do something like that, the effort fizzles and the group fades.
Also this potential "linkability" factor you mention can be associated with that group anyway... thus adding a potential dimension of profiling which is probably not desirable either, even though it may help obfuscate other dimensions of profiling as you point out. Ultimately, I'd say the trust factor and group association aspect (plus the fade factor I've experienced) combine to negate the potential benefits.
I think you'd do better to take advantage of the many domains that are available at some hosting providers such as FastMail (which has dozens of optional domains for aliases) or use something like SimpleLogin and use their domains, and/or mix it up with some of your own domains spread around at different providers you trust.
The profiling algorithms are very complex and track all sorts of info about you, as I'm sure you know, down to your computer/device fingerprint, so you'll never 100% get away from it, but you can spread yourself around and use services that have better privacy policies, use blockers, VPNs, etc., and use various alias options out there and it can help to some degree. Good luck with it and let us know what you decide to do!
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