One speed limit on your ability to upgrade your systems
[...] it's not "pain" - it just doesn't happen. At 2 weeks of planning + testing = 26 systems per year
This was eye-opening in a 'I hadn't thought about it that way before now' way. Like many insights, it's blindingly obvious in retrospect; of course how fast you can actually do an upgrade/update cycle determines how many of them you can do in a year (given various assumptions about manpower, parallelism, testing, and so on). And of course this limit applies across all of your systems. It's not just that you can only upgrade a given system so many times a year; it's that you get only so many upgrades in a year, period, across all of your systems.
(What the limit is depends very much on what systems you're trying to upgrade, since the planning, setup, and testing process will take different amounts of time for different systems.)
To upgrade systems more frequently, you have two options. First, you can reduce the time an upgrade cycle takes by speeding up or doing less planning, building, testing, and/or the actual deployment. Second, you can reduce the number of upgrades you need to do creating more uniform systems, so you amortize the time a cycle takes across more systems. If you have six special snowflakes running completely different OSes and upgrading each OS takes a month, you get twelve snowflake upgrades in a year (assuming you do nothing else). But if all six run the same OS in the same setup, you now get to upgrade all six of them more or less once a month (let's optimistically assume that deployment is a snap).
I see this as an interesting driver of uniformity (and at all levels, not just at the system level). Depending on how much pre-production testing you need and use, it's also an obvious driver of faster, better, and often more automated tests.
(Looking back I can certainly see cases where this 'we can only work so fast' stuff has been a limiting factor in our own work.)
Spam victims don't care what business unit is responsible for the spam
So what happened is that the other day I got some spam that our MTA received from one of the outbound.protection.outlook.com machines. Since sometimes I'm stubborn, I actually tried reporting this to firstname.lastname@example.org. After some go-arounds (apparently the Outlook abuse staff don't notice email messages if they're MIME attachments), I got the following reply:
Thank you for your report. Based on the message header information you have provided, this email appears to have originated from an Office 365 or Exchange Online tenant account. To report junk mail from Office 365 tenants, please send an email to email@example.com and include the junk mail as an attachment.
Ha ha, no. As I put it on Twitter, your spam victims don't care about what exact business unit is responsible for the specific systems or customers or whatever that sent spam. Sorting that out is your business, not theirs. Telling people complaining about spam to report it to someone else is a classic 'see figure one' response. What it actually means, as everyone who gets this understands, is that Microsoft doesn't actually want to get spam reports and doesn't actually want to stop spam.
Oh, sure, there's probably some internal bureaucratic excuse here. Maybe the firstname.lastname@example.org team is being scored on metrics like 'spam incidents processed per unit time' and 'amount of spam per unit time', and not having to count this as 'their' spam or spend time forwarding the message to other business units helps the numbers out. But this doesn't let Microsoft off the hook, because Microsoft set these metrics and allows them to stand despite predictable crappy results. If Microsoft really cared, outlook.com would not be the massive spam emitter that it is. Instead Microsoft is thoroughly in the 'see figure one' and 'we're too big for you to block' business, just like a lot of other big email providers.
(For people who do not already know this, 'see figure one' refers to a certain sort of grim humour from the early days of Usenet and possibly before then, as covered here and here. The first one may be more original, but the 'we don't care, we don't have to, we're the phone company' attitude is also authentic for how people read this sort of situation. Application to various modern organizations in your life is left as an exercise to the reader.)