It's one of those weird paradoxes. On the one hand, what you're saying is absolutely right. There are all kinds of affordable options and new players entering the market. But in a way that's also the engine of the problem, because there's so much going on it's now confusing to newcomers just where to start. So they look for advice from people who are into the hobby...
...and that's where they run into the subjectivist bias. They might not be able to read a set of measurements at first, nor will they have experience with similar gear to what they're looking at to make comparative impressions useful (e.g. "It's like an HD 600 with more bass"), but they can understand "I bought this $$$$ amp and it made a night and day difference!" just fine. And once they start reading that kind of statement over and over, they'll most likely do one of two things: either they'll conclude they've wandered into the insane asylum by mistake and back out of the hobby entirely, or they'll assume that since everyone is saying it, it must be correct, so they'll start believing it, too. I wonder how many people who were attracted by the inexpensive gear ended up not buying any of it and just leaping right into the more expensive end of the pool just because they read so often that they need to spend more money?
I'm not saying having more options is a bad thing. It's a great thing. But it can be hard to separate the wheat from the chaff with so many choices, and with practically everything becoming a FOTM and the snobbish types looking down their noses at anybody who doesn't spend tens of thousands, I don't envy newcomers one bit trying to make sense of it all.
This is where I wish people like Tyll would look at inexpensive gear more often. He tends to stick with mid-priced and flagship-level stuff, which is understandable given the audience for IF. But for somebody just starting out, "mid-priced" these days is still at least three or four hundred dollars, which is more than they're likely willing to pay upfront. The WoF is a good place to start looking, and of course once you've heard enough gear you can get a rough idea what to expect from the measurements section. But it's still dominated by stuff from the upper end of the price spectrum, and the lower end gear on there consists mostly of old standbys. The PortaPro is decent for what it is, for instance, but I have to believe that there's something better (or at least which strikes a different set of compromises) lurking out there somewhere these days.