ive been in IT for 6 years, and started with an MSP where companies would hire us for IT support. They would still be using shit like Office 2013 and we'd do insane shit to get it setup for Office 365 accounts. My company luckily pays out the ass for proper software so Office is way more reliable. It really always comes down to how fucking cheap a company wants to be, and when I did support for non-profits they were always cheap as fuck. We'd spend so much time fixing stuff that certainly could be alleviated with money. But a shitload of companies don't see IT as an asset. I am lucky my company does at least. Plus most of our shit is single sign on.