Wow a little harsh, don’t you think? Maybe I should have used the Toyota Corolla instead? These weren’t trendy vehicles when they were new, that’s my point. Perhaps you missed the part of my comment where I prefaced with “If your fortunate...”? Because obviously this was an off-topic side comment countering GPs generalizing that all cars necessarily lose value, not a strong claim about the market as a whole.

I can't speak to the VW but the Tacoma was absolutely trendy when new. From 2000 or so to present it has been the official pickup of "I don't 'need' a pickup but I make good money, I like nice things and I want a pickup" (I'm not saying there's anything wrong with that reasoning). They've always (even back to the 80s and 90s) been more expensive than the alternatives when new so only people who are dead set on them tend to get them.

They're comparable to the Jeep JK and the WRX STI or a performance trim Mustang/Camaro but for different demographics. Anyone could tell you that they would hold value better than average when new.

Losing less value than average is not all that remarkable. Gaining or failing to lose value is exceptional and subject to the whims of consumer culture (see my tangent about diesel pickups). Jeep Wranglers used to be like that but as the 4dr JKs hit the used market it calmed down a lot. Old full size Broncos are probably about to stop losing value if the rumors of a new fullsize are to be believed.

Also I toned down the language in the original a little.

Are you sure you're not mistaking it with the later post-2004 models? The early model MSRP'd at <$20,000 ($26k today infl. adj.) and was a small pickup, nothing like the full-size $45k beast that is offered today. It would be odd to compare it with the $35k WRX STI.

Anecdotally, I purchased a used Tacoma in 2011 for a few thousand dollars as a family workhorse vehicle. I sold it for nearly double five years later with only making regular oil changes. This really changed my impression of the used car market and have since started a side hobby buying and restoring "almost-classic" vehicles.

I'm not comparing it in terms of cost, I'm comparing it in terms of how buyers think about it. People buy a WRX STI not because they don't know what they want and it seems reasonable. People don't buy a WRX STI because they want a sedan, do a bunch of number crunching and decide it's the best fit for their needs. People buy a WRX STI because they're in the market for a sedan and they want a WRX STI. The same is true for the Tacoma and a whole host of other vehicles. People buy a Tacoma because they specifically want a Tacoma and they pay out the nose for it (especially if buying used).