Reminds me of a job I left years ago after the company got bought out. The new CEO was a nightmare. It was an official policy that weren't allowed to disagree with him or even offer alternative solutions. I witnessed so much insane garbage there I don't know how his company ever became successful.
All of our sites were connected via MPLS. It worked fantastic for our needs and we rarely had problems with it. They were using 10 year old hardware devices to build VPN tunnels between each site. It dropped the tunnels so regularly they had everything redundantly built at each site. A clusterfuck of DFS to try to keep each file server in sync, Exchange servers at each site, etc. Their solution was have us get rid of MPLS and buy their VPN hardware off ebay to link all sites. By the time I left, he decided that wasn't working and every location would upgrade back to MPLS but use the cheapest provider at each location and IT would have to find some way to make it work.
All of their servers were homebuilt white boxes. When they would need a new one, it was built with what was cheapest at the nearest computer store that day.
Exchange and domain controllers were running in multiple different versions across the company. There were zero standards in version or config.
They ran two different AD forests and each user had two accounts for "increased security." One was used when logging into their computer and network access, and the other used only for email. People often had two different usernames. John Doe might have JDoe to log on his PC, but JoDoe for email because Jane Doe has JDoe for her email already.
Because usernames were so difficult to keep track of (again multiple forests for increased security) all network file storage was set to anonymous access. Anyone on the network had full control to any file.
All of our PCs and most servers had completely automated loads. This was deemed inefficient and we ripped it out to hire techs at each site to manually reload computers whenever requested. The same was done with all software.
Our VPN solution for home or traveling users was a "security risk." Anyone wanting remote access would be assigned a laptop and a specific public IP that would then be forwarded to their desktop PC so they could remote control it from anywhere.
The CEO misheard the Agile development method and called it Argyle. All internal communication and training had to replace Agile with Argyle to avoid anyone having to correct the CEO.
We had dev and staging that our developers used that was considered a waste of time. They were given full control to our live servers, which led to constant downtimes. For example, one dev found some new authentication module to supposedly help PHP authenticate against MS Active Directory of some dude's personal wordpress blog and replaced our live working system with it. When no one could authenticate anymore and things went down we had to have a meeting about how we could have prevented causing this problem for the dev.
Don't pay for any software. If you can find a cracked version use that.
Our DR site was scrapped because it was a waste of money to have redundant servers that weren't being 100% utilized and just waiting for something bad to happen. You can always just run to Best Buy and build a new server if you need one.
The list goes on. Every department was the exact same way with everyone running around like a chicken with their heads cut off receiving new directions daily that would conflict with the previous day.