This is exactly right for multi-family housing. I can't see any sort of startup or disruption coming in anytime soon without taking years of hard work to reach 50% feature parity to meet what the industry expects are standard features. (Or maybe I've been working here too long to get past that notion.)
What exactly is shitty about it? Old browsers can still display text, images and hyperlinks. There are millions of use-cases perfectly covered by them.
For starters, users expect modern-looking websites. That includes users on old browsers, thanks to the amount of bending over backwards done in the web industry to provide those users with as much of the modern browsing experience as possible. If you serve up a page looking like the c2.com wiki to a non-technical user, they're not going to be too happy about it.
Far more so than that, though, what's shitty about having to support IE 6-8 is the complete lack of consistency. Even if you aren't doing anything fancy, you have to spend a hell of a lot of dev time if you want things to look the same across browsers when they're included. Hours and hours of wasted time is pretty shitty, especially when the work involved is so aggravating and, from a creative point of view, utterly pointless.
In effect, your question is like asking what would be shitty about developing apps for a 10-year-old Palm Pilot. There are millions of use-cases perfectly covered by those too, but that doesn't mean an iPhone app developer is going to want to spend time porting his apps to one.
Even if the users expect "modern-looking" websites - it is not something that cannot be done with IE6.
Secondly, you don't have to design 1:1 pixel-perfect copy of your website that looks the same on all browsers.
The main thing - if your developers cannot degrade the website functionality - they are seriously doing something wrong - get more experienced
You can as well design Flash site and call it "progress" and tell the rest of our users to go somewhere else. Now, how is it different from other "modern" technologies? Its W3C support?
"but that doesn't mean an iPhone app developer is going to want to spend time porting his apps to one."
If your customers still use Palm Pilot, then why would you design your site ONLY FOR IPHONE??????
The developers always can degrade the functionality; whether they can is not the point. The point is how long it takes them to, and how much they could be doing for other users with that time. Getting more experienced at making products that work on broken platforms is not a good thing. That is not good experience. That is a symptom of a broken industry and it makes your developers worse, not better. It's like people who say PHP isn't that bad, you just have to learn all of its quirks. Learning its quirks doesn't make you a better programmer, it makes you a programmer who is able to use a specific poorly-designed tool. That experience and knowledge is not portable and is not valuable outside of a specific arena, and is not the kind of experience and knowledge that developers should be working on.
If your customers still use Palm Pilot, you've chosen the wrong market segment. Yes, make something people want, but you're allowed to be selective about who those people are. If you're a hacker, it's very likely because you enjoy creating and working on interesting and fun things. Making websites work in IE6 is not a fun thing. There is enough value waiting to be created that we don't have to waste our talents and energy on this kind of nonsense.