I’ve been through 2 big clear-outs. One in the mid-90s and one in the mid 2000s. I did regret selling some of the gear in the second clear-out, like the expanded Supernova 2. Emu e5K sampler (with RFX32 card and various bells and whistles) too.
I ended up re-buying some of the kit, but I couldn’t necessarily find the same expanded versions. I’m very glad I kept some stuff though, like the Korg Z1 (which has the extra voice card).
Selling my old Korg Workstations though, is something I’ve never regretted. I’ve been through Trinity and Triton Extreme. I was only using them for traditional keyboard gigs, so moving up through to Kronos - haven’t had any problems finding patches which work.
I’ve now got to the point though, where I’m seriously considering selling a good chunk of my Elektron boxes. My work-flow is better with a centralised sequencer (Cirklon or DAWs) and tbh, I’m not overly impressed with the raw sound of some of the Elektron toys. The Elektron magic, usually happens when the sound engines are combined with the on-board sequencers.
I’m waiting to see if the new OB suits my work-flow, otherwise there might be various bits up for grabs.