I tend to agree that when it comes to specialized tools, there are a variety of ways to approach purchasing. But a router, in my opinion, is one of the "staple" tools for any hobbyist, craftsman, or carpenter who will work with wood in their lifetime. Along with a router, a power drill and a circular saw are pretty much all the power tools that are truly required to do just about anything. It is one of the few tools I would never consider buying cheap.
PLUS, a router spins at 10-30 THOUSAND RPM! That is a tremendous amount of rotational energy, even with a small bit, and I for one would never stand near (let alone hold) a tool that was made with the lowest possible quality materials, labor, and quality control standards that contained that much potential energy. I value my fingers and skin way too much for that. But that is my opinion, other's may see things differently. (I have not personally lost anything larger than a chunk of flesh from a power tool but I have witnessed tool failures causing great bodily harm in my life).
As for your example with the drill, I understand, and I can't say that you went the wrong direction with that. However, quality tools hold their value more than just about anything else you can purchase (that you would use, there are plenty of things you can buy and never use that will hold value). My table saw, for example, is just a simple Delta contractor saw (at least the base is, I have modified the rest to be much more). About 25 years ago it cost around $300 to buy brand new. I purchased it 13 years ago for ... $300. Today, I could put it back to its stock form and sell it for $300+ quite easily. Aside from cordless tools which have become so common (and have batteries that degrade over time and use), any decent power tool will have a fairly static value from the day you buy it. You could argue that with inflation I have lost value in those tools, but the fact is if I hadn't bought those tools, that money would have ended up being spent elsewhere, and likely on something that is worth far less today. You could also reasonably argue that buying a tool brand new is like buying a car brand new, and the moment you take it home it loses a big part of it's value. This is true, but it is fairly minimal, and also a good reason to buy used to begin with.
While newer tools tend to be "technologically superior", they also tend to be built far "leaner" (which translates to not lasting as long) and people will often pay for the older gear for that very reason. I would kill to have back some of the older tools I traded off for newer "upgrades" that turned out to not be nearly the same quality as the older items. I suppose that is one reason to buy the cheapest stuff you can find the first time around... when you go to upgrade, no matter how far it falls short of what you thought it would do for you, it will still always be superior to what you had, lol.