Resale value

Sure, whatever! 

In evaluation the "value" of a component I do consider the enjoyment it will bring as part of the "equation".

Having said that, I find that all audio equipment depreciates fairly quickly, so I've bought a number of "current model" components from individuals who seem to like to try out new things for a few months, like a new car purchase, the ones who "take the hit" on the depreciation.

I prefer to purchase used items from individuals, compared to "dealer demos", as when I worked in the audio business, I found that our components had lots of hours on them, by the time we sold them.  You oftentimes do benefit from the manufacturer's warranty when you buy these components, but when the staff power the units on when they open the store and leave them on all day, they do have a lot more "wear" on them by the time you purchase them as a demo unit.

I also have "a thing" about buying used speakers.  To me it's really difficult to figure out if speakers have been "abused".

One thing I've found is that McIntosh components seem to hold on to their value better than other brands.

No, I don't consider resale value until I'm prepared to upgrade or sell an item.  I only consider the need to upgrade to a better piece of equipment to fill a gap or issue with my system. 

That said, since my music taste and system make it relatively easy to determine if equipment is performing to my expectations, I typically demo higher end equipment before purchasing.  I find it incredible that some dealers will not allow potential customers to home demo high end equipment for a short period before purchasing.

My favorite dealer in San Diego would allow me to take equipment home for a week or so.  They would take my credit card information just in case. 
But, at this level, you really have to hear it in your home and system.  In the store, isn't nearly the same.

So, buying and not being satisfied and quickly selling doesn't strike me as being something I want to look forward to.  Especially for really costly items.

Now if you bought the item for pretty close to blue book value, then no worries.  but, if you bought the item for close to "retail" value, then each time you're probably taking a loss on resale.

That may be okay if you owned the item for a long time, but if you purchased it new based on listening in the store, of someone's recommendation and took it home, connected it and it sound like crap after the appropriate break in time, well, that just sucks.

I purchase to fill an deficiency in my system, or I can afford the upgrade. 

Enjoy

Short answer is no; if it's something I just want to try out I try to make sure it's priced right; if it's something I am reasonably certain will be a significant improvement, I only consider the "marginal value" of my increased enjoyment.  

When buying gear, I consider resale but it's not a deal breaker if the product has a low resale value.  Me, I buy name brands, from companies that have been in this business for a long time with outstanding customer  service.  If that means, I save longer for something new, so be it.