Also, if you're making a substantial site with, say, 10 million MAUs, 5% of them is 500,000 people. That's a lot. Do you really want that number of people telling their friends "The site doesn't work for me"?
I could not care less.
Go where your customers are. If you don't have customers, do what you like. Although I'd question whether you even need a website if that's the case.
I am not downloading GBs of VMs and spend hours of time to validate IE for a couple of illiterate smugs.
;)
But that has to include the all the customers, not just 97% of them. Start with the low-hanging fruit of course, but never settle for "those customers are too much effort to bother with". That sort of negative sentiment is toxic.
I, and many others, do care. It is appreciated someone else sees the bother.
We have a set of users who are using our site in healthcare environments, on locked-down computers that are difficult/expensive, so in some cases they're stuck on IE7/IE8.
I'm pretty sure calling them "illiterate smugs" wouldn't go over well.
On the other hand, these computers don't have access to the general internet, so in this case they don't risk running afoul of site creators who decide to be "clever" and go out of their way to aggressively (or even insultingly) demand that visitors upgrade. But restricted corporate users who hit that sort of thing would be unamused.
Don't encourage them by supporting old IE's.
And on the flip side, a lot of those employees are a sizeable chunk of business for other businesses when they browse on their lunch breaks or whatever. So, large sites aren't going to fully drop support for any browser until after the market share has dried up.
Firstly, the policy is there for a reason -- often something like "we paid a lot in 2003 for this custom software, and if we upgrade browsers we'll have to pay X to have it rewritten/replaced".
X may be a rather large sum of money -- easily enough to overwhelm whatever benefits they might get by becoming paying customers of whoever's new venture.
There's also a potential for a sort of catch-22; new sites/services may pop up that could even replace their old custom-built software... but if they can't even try it out and the site looks awful on their browsers, a) it's less likely they'll make the jump and b) it gives the impression of being a new-fangled flash-in-the-pan sort of thing. After all, the serious companies online put the effort into supporting older browsers.
I know that customer requirements are pretty much unheard of in startup land but other companies have to obey this kind of limitation in order to make any money (which again is an alien concept in startup land -- not every business model survives on growth alone).
If your site depends at all on user generated content (even comments), one active desktop/laptop user is probably worth hundreds or thousands of screenboard users. On my non-corporate-facing sites, IE is still 30+% of desktop usage, even though it's only 5-10% of overall usage.
Also, if you provide an untested experience to your IE users, you're probably bouncing many more users than you realize. Very few people return to a site that doesn't work in their default browser.
nb: I'm typing this in Chrome on a MBP.