@Otto -

Otto,

You hopefully know how much I respect you, and I think we’re both fully aware that we’ll never see eye to eye on everything ;) but I think this is a really great microcosm for the disparage between us :)

1) R U SRS Bro?
We have a singular functionality, with a sole purpose to detect a user’s browser and tell them if it’s not the latest version, and... it doesn’t work.

“problems with browser detection and so on are well-taken”

I really appreciate your openness about this, as always, but come on. Given that most of the time this functionality fails with people using IE, and that the target audience is for... people using IE; doesn’t make this piece of functionality Not Fit for Purpose?

It’s a browser detect that can’t accurately detect browsers.

But we're not making any attempt to fix it because, well it can't target people on Macs, so who cares...

2) Upgrading and the Veil of Ignorance

I realize that you don’t like the whole idea of upgrading, but it’s a fundamental fact in computing that isn’t going to go away just because you and your clients don’t like doing it.

I apologise if I’ve given you the idea that I don’t like upgrading, or being on the latest version appropriate of whatever software I’m using, I’m personally a bit of a beta bunny.

But the rest of the world is not. If it was would we have to do all of this? Um... I’m being vague here to stay within NDA: One of my current clients received close to the same number of hits as Amazon and eBay last year (outside of Christmas and some holiday y’all have in November), and will probably do similar this year (maybe a little less). 41% of their traffic in the last 12 months came from people in WindowsXP. IE6 and 7 made up more than 30% of the browser share.

I absolutely understand that’s just one website, but when comparing those numbers to the 500+ other websites in the company, the percentage of WindowsXP and IE6/7 didn’t drop below 40 and 20% respectfully.

I fully understand that this is somewhat anecdotal, and it’s just one website, I do get that; but when those of us out in “the real world” are looking at that sort of statistic over and over, from site to site, from company to company, from country to country, it’s hard to get behind this idea that it’s just me or my clients that don’t like doing it.

3) OS upgrading

Windows XP is 10 years old, and will be at its end-of-life in a bit over 2 years from now. It’s time to upgrade your OS too.

So I agree with the premise, but that argument isn’t really what people hear. To start with, end-of-life means nothing to the man on the street. What they hear is this:

Windows XP is 10 years old, and Microsoft will no longer support it in a bit over 2 years from now.
It’ll still work in the same way it does now, and the way it has done for 10 years, but it won’t be “officially supported”.
You therefore have a bit over 2 years to pay to upgrade to the latest version of your Operating System, which will cost you about $100 – but if you pay for it now, note that you’ll not be on the latest version of the operating system next year when Windows 8 comes out.

That’s what people like my Mum hear.

When we techies hear 10 years old we think “holy crap I need to upgrade” but non-techies think “wow, that’s really stable, I’ll stick with that”. When we techies hear 2 years until end-of-life we think “holy crap I need to upgrade” but non-techies think “wow, that’s far away, I’ll save my money and maybe get something closer to the time”.

4) The bubble

So this is where we’ll disagree the most I think. We have 20,000 people who make a living from WordPress (according to your boss) – that’s an awesome number.

But it gets harder to really sell WordPress to both individuals and companies who are resistant to change. I understand “Adapt. Or Die”. I’m a certified and practicing Scrum Master, Product Owner and Practitioner – I understand the premise of Agility from Darwin to XP programming. But it’s really hard to go into a company – of any size – and see people using IE or Windows XP/Vista, or have disabled people, or blind people, or know they current have an IIS server or any of the other types of people we’ve moved to edge cases we don’t really like; and attempt to say hand on heart, WordPress is the right software for you for the next 2 years.

And I think thats the bit that you’re missing bro. If you/the-core-team/matt/Automattic/WordPress all don’t want to support IE6, IE7, WindowsXP or anything else – I’m ok with it. I may not agree with it, it may result in me using WordPress less, but it’s not my call. But how many users of WordPress, or any software, like being told off and having something added to the software they’re using that reduces the User Experience. It doesn’t come across as attempting to be helpful, it comes across to the end user as being an arrogant superior techie jerk.

It’s hard to want to use software that constantly moans at you for something you may not be able to change.

5) Finally

If I may, another Anacdotal reference...

My mother, a woman who used to code Pascal and Cobol, but really never liked computers (yeah, I know) recently asked me to uninstall that "web thing, that kept p*ssing her off by telling her to upgrade constantly when [she] only upgraded last week".

So Firefox 7.0 was removed from the computer, and she's back using IE8.

Efforts to move her to Chrome or IE9 were met with: "But doesn't [ie8] do everything I want it to do?". I had many arguments for IE9, but you know what, IE8 does what she needs it to do, and it already is on her machine, and it works. Sometimes, we techies focus on the cool new things a bit too much.