Interesting to hear if so. Whether it is an old Fender guitar or an old Synth or even anything to do with the musical studio. Lets single out those gems. I have bought and sold over the years and regretted as some have gone through the roof in value. Including a Yamaha CS80. Heyho hindsight is a wonderful thing.
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So far ASR-10 (which I just sold for almost triple what I paid, thank you Kanye) and SP-303 (thank you Dilla, Dakim and vaporwave). Waiting on my Quadraverb and Alpha Juno 2 to start inching up (doubt I’ll ever sell). I need to fix my Tascam 144.
Nothing dramatic. I sold my OP-1 for a couple of hundred more than I paid for it new. Apart from that, Monomachine mk2 I guess - that’s never being sold though.
Lots. The price of a VCS3/DK2 keyboard is crazy these days - 8 times what i paid for mine. Minimoog, Prophet-5, 2600, PPG Wave 2.2/Waveterm… most of my vintage stuff has gone up in value. Some wasn’t ‘vintage’ when I bought it.
However, the list of synths I regret letting go is far longer…
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CS-80! ouch.
I’ve been toying with getting an alpha for the past year or so and prices are steadily rising, at least here in the UK anyway. A long way to go before they’re worth more than they cost when new but all the rave nostalgia going on right now is definitely inflating prices.
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I had a MicroKorg a few years after they were released. Had it for about 5 years then sold it on ebay for £5 less than you could buy one brand new. Go figure 
SPS-1 UW Mkii +
SFX-60 Mkii +
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…oto bisquit…
doubled in price for a second hand unit, compared to it’s price once new these days…
funny enough, just found out that on mine, the GAIN poti does not work properly anymore…
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MM mkII+
Guild Starfire IV - original from 1964.
I’d never sell these because to me they are just too wonderful. If I go totally blind and deaf or my hands drop off I might consider it.
I’m not so interested in things that gain value but I remember buying the A4 mkI when it was released as one of my first more expensive purchases and thinking it’ll at least hold it’s value haha…
I think what is more important now is whether something gains in value in terms of ‘use’… The financial side of things is bullshit.
I have a Selmer Super Action 80 Series ii Tenor saxophone that’s worth about 3x what I paid. I got a steal, so technically, it’s just held its value.
I’ve had it for almost 20 years.
I have a few bits worth more now than I paid, mostly vintage Roland stuff, but I have sold lots in previous years that had I kept would have been worth many times the amount they cost me.
I don’t really care, I value them in terms of what they are worth to me rather than monetary value, they are instruments not investments. Also I don’t think a lot of vintage gear is worth what they are selling for, but the same can be said of most vintage items because demand is higher than supply and there is always someone willing to pay top dollar for a nice example.
I do think people fetishise vintage gear a bit too much, even some stuff which was considered pretty mediocre back in the day, but by the same token there are still plenty of sleeper items which have not yet been subject to the same level of hype and can be found at quite reasonable prices.
Overall though I mostly prefer modern gear nowadays, but not exclusively.
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Crazy how expensive synths were back in the day, even if they have increased in value. According to Wikipedia, the VSC3 sold for 330 GBP in 1969, which is $7,000 in today’s dollars when adjusted for inflation. I can only think of one synth today that costs that much new: the Moog One.
Edit: Of course, if a person had invested the $7,000 in stocks instead, it shows how poor of an investment instruments are. If a person in 1969 had invested the $7,000 in Disney stock, for example, it would be worth $3.4 million today - a little better than what a VSC3 goes for today.
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Selmer Mark VI saxophones are worth about 10 times today what they were 50 years ago.
Had a Tanzbar some time ago. Got it for about 400Euro. When I sold it, the street price for second hand Tanzbars were around 700Euro, so that’s what I got for it.
My MonoMachine.
Also sold my FS1R for far more than I bought it for.
(anyone who bought a Nord Drum 2 over 2 years ago)
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Got a used op-1 for 700€ just a few months before TE offered the new batch for 1400€. 
I sold a monomachine sfx6 years ago for about what I paid for it, but not for the price that the monomachines are sold today. Also sold my EHX memory man too early and years ago for about half the price today (they go now for 500 EUR). So its more like not having to pay on top of what i paid.
I know nothing about the Nord Drum 2. What makes it sought after?
Edit: Never mind. I see from Nord’s site that it offers a lot: substractive and FM synth drum sounds, six channels, easy to hook up to pads, tweakability, etc.