Resale value

I can't believe tonykay and cleeds are arguing about the stock market and liquidity come on guys relax it's  stereo equipment! On the subject of resale value while I don't strictly consider it I do feel like I have a pretty good sense of what is and is not a good deal on here. Another way of saying I spend way too much time browsing the listings! The upshot being I've never seriously taken a bath on anything and I've never not been able to resell something after a purchase. I think after a while it just becomes instinctual. And I have mostly bought and sold gear from smaller companies with no issues.

More power to you if you buy without caring about resale.

i have too much invested into this habit that I need to have an "out" just in case.

Very interestimg comments all around. I would love to buy really boutique stuff, but I notice that it tends to stay up for sale for long periods or is reposted for sale at later dates. Guess there's so much great sounding equipment from well-known makers (which tends to sell relatively quickly), that it makes little sense to me to buy less marketable items. The idea of having a fast "out" should the equipment not work for me is very appealing.

If you purchase a great sounding unit others will know its a great sounding unit from multiple different reviews by various audiophiles. 
Safe to say that if you sell it people will buy it. 

To answer OP, never, ever.