I would be interested about an economically formalized approach to this! I am often confronted with similar decisions, trading off time vs money, taking into account friction, and I am usually unsure how to put it into some sort of an equation.
To build my own server, I read the very useful thread here: Making your own server - #420 by superMDguy
I then settled on a parts list by using pcpartpicker: https://pcpartpicker.com/list/kxWVXH
Software-wise, I set up Ubuntu 16.04, and installed all the python modules in dedicated Anaconda environments (one per course since they use different versions), which has been extremely smooth so far.