At this point with me having more guns than I "need," the hunt for the next gun is often a significant part of the enjoyment and satisfaction of acquiring and having the gun. Gun acquisition is a more complex hobby for me than just "buying a gun" and having another one in my safe. The thinking-about-it and the searching for the right gun is something I enjoy, and is a stress reliever.
Most of the guns that I want these days tend to be in the 10 - 70 year old range, so in those cases I'm not just looking for the best price and availability on a NIB gun. I tend to spend time, and get enjoyment from, deciding which gun(s) I'd like to have, determining if there are certain year models or versions that I think I would enjoy owning more than other versions, and then finding that gun at a good price. A "good price" almost always means a price at which I could sell the gun and make money. I don't look at guns as an investment, per se, but I try to buy for less than I could sell just because I like knowing that the hobby isn't a money pit.
This is how I approach it, and how I get enjoyment from the hobby for me, but it's not to say that it'd be for everyone. If I looked at the gun hobby differently, I might see guns more as "tools," in which case it probably wouldn't make sense to search out my own personal Goldilocks gun every time.