[jamespcole2]

It's mainly things like the lack of a good package manager for provisioning, inexplicably large installers, sub-par automation, inscrutable GUI's packed with useless features, having to RDP into a server to perform basic tasks rather than just using SSH, massive bloat(why is everything so huge?), a general disregard for dev ops.

Also I find the licencing really irritating when creating VMs and servers. In the end thinking something "feels" old and clunky is a subjective perception but every time I use MS products it feels like they were created with little or no insight or knowledge into what anyone else is doing, leading to a lot of NIH syndrome.

Absolutely garbage browsers are also a big problem, I know IE 10 is passable but in 4 years when it hasn't been updated and people using Win7 and 8 are stuck using it, it will be the IE6 of its day.

Don't get me wrong, I used MS products basically exclusively for the first 5 years of my developer career, and still use them a fair bit now, and thought it was amazing, it's not until you move outside that bubble and start using better tools and methodologies that you realise how far behind they are.