I've had my Yahoo! account since late 2000 when I signed up in order to learn something, anything, about Yahoo!'s services prior to my job interview at Yahoo!.
Inertia meant that even after I was laid off in October 2008 I kept using Yahoo! Calendar.
Over the past few months I noticed that Yahoo! Calendar was no longer sending email reminders consistently. I couldn't figure out why and kept checking the calendar entries -- indeed the email reminders were ticked for every item.
It appears that the Calendar UI shows email reminders as ticked but this is not reflected in the backend. I say this because when I exported all of my calendar entries as a giant ICS blob all of the calender entries from many months ago have the relevant reminders but recently created entries don't. Yet both show reminders in the UI.
I can't fathom beating my way through customer service to report such a bug -- cue the pre-canned responses suggesting user error -- so I began thinking about alternative calendar services.
Google Calendar and Outlook.com Calendar are obvious candidates but I would end up in the same situation -- all software has bugs and I'd have the same experience attempting to report bugs to Google or Microsoft.
In fact, in 2010 I had a paid Google Apps account and encountered the slow Gmail bug of 2010 as reported by Gabriel Weinberg of DuckDuckGo fame. Except not being e-famous we were unable to convince Google of a problem even after submitting the packet captures they requested. They simply went silent. Simple solution: close account and move to a provider who cares (in this case, Rackspace email, so far so good).
Thinking about how I should choose my future calendar provider brought me to the realisation that if there is a service I rely on I'd rather pay for it and have the ability to contact support than use it for free and have no support (or useless support).
Hence I have opted to sign-up with Fastmail. They're better known for their mail service but recently added calendars. They're also known for being technically astute and sound like the sort of company I could rely on - small enough to care, large enough to be financially viable, and seem to have the desire to be in the mail/calendar game for the long term.
It'll cost me $40/year but that's peanuts compared to the time I would have to spend convincing a Yahoo!, Google, or a Microsoft service person that there are technical issues with their products.
Of course paid vs free and good vs useless support is not a causal relationship. But in my experience they are highly correlated and generally companies tend to care more about paying customers than free ones. Looked at another way, companies tend to care more if you terminate your paid account than when you terminate your free account.
Also, this post isn't saying that free has no place in my world. Free is fine, when quality doesn't matter.
I'll continue to use free services from Facebook and Google because they're not critical services in my eyes. It won't really matter to me if they died tomorrow. Flickr is a weird case because I used to pay for Pro but Marissa decided to make it free. I guess if it dies I'll look for a solid paid photo host. I have paid for SmugMug in the past but found their product clumsy.
On a related note - Yahoo! Travel folks are spamming newsletters to some out-of-sync list. I've unsubscribed god knows how many times over the past few months and unticked every marketing thing I can find in my account. I'm pretty much at the point where I'm just going to bin all Yahoo! emails and I guess if my account gets hacked at some point in future and they try to notify me I won't get it. I'll simply no longer be a Yahoo! user at all -- including Flickr.
I feel like there's a reverse network effect in here somewhere. That the poor performance of the Yahoo! Calendar and Travel teams will inevitably cause the loss of an otherwise loyal Flickr user. And in the mean time I will have changed my thinking of my Yahoo! account to Yet Another Account I'll Probably Lose In Future So Don't Use It For Anything Important.
Lest anyone think I'm just jumping on the Let's Rubbish Yahoo! bandwagon, in a strange twist, I am still a YHOO shareholder (reasons below), and as I said above the same problems apply to Google, Microsoft, and many others.
When I was laid off I had a bunch of RSU and ESPP shares that were below water. Being the height of the so called Global Financial Crisis I worked out the sum of parts and it seemed to me that Yahoo! Inc was valued below its components of Yahoo! owned and operated subsidiaries, shares in Yahoo! Japan, and shares in Alibaba.
Irrespective of what the market may think of their products and prospects Yahoo! Inc, even today, throws off over a billion dollars in free cash annually. I don't have to be a Yahoo! user to consider it a reasonable investment for the short-medium term.