Our boss said that developers should have fewer mistakes so the company would have money for displays, servers etc. An always mentioned example is a late firing of an underperforming colleague whose salary would have covered some of these expenses.
On the other hand it happened a few times that it took a few days to free up some disk space on our servers since we can't get any more disk. The cost of mandays was definitely higher than the cost of a new HDD.
Another example is that we use 14-15" notebooks for development and most of the developers get external displays after they spent one year at the company. The price of a 22-24" display is just a small fraction of a developers annual salary.
Devs say that they like the company because of other reasons (high quality code, interesting projects etc.) but this kind of issues not just simply time-consuming but also demotivate them. In the point of view of the developers it seems that the boss always can find an issue in the past which they could have been done better so it's pointless to work better to get for a second display/HDD/whatever.
How can I convince my boss to invest more into development environment? Is it possible to break this endless loop?