I have worked in IT for 10 years. It depends on your current knowledge and how quickly you are able to pick things up. If you want to go down the support route which is what that other guy is doing. Most support jobs will be in an office and not from home. He probably has a job with an IT company that sells out of hours support and he potentially works on 100s of clients that only calls when they have issues, depending on the support contract of course. He is able to work from home because he does the night shift, usually the person would be placed at clients sites during the day. Although it is possible he is in a team of people that work remotely, as these days that can be more common. However a lot of issues still require hands on but not as much as the past. Even physical servers can be managed with ILO. A lot of companies are moving to datacenters with high security and permitting guests to work on issues all the time doesn't make sense.
In terms of what to study. There are different routes, general support and operations, specialist, management, sales, procurement and so on. If you want to go in to general support and operations then you need to learn windows server and vmware and enterprise storage and the applications that enterprise and business use and how to deal with network printers and VC and so on. If you specialize you can then try get a job only upgrading exchange email server for example.
I do know some programming however, never went in to development but have worked within development environments. I think being a developer is better than operations and support. The developers have more freedom have to deal with people less and they are better paid and more appreciated. Developers are considered closer to marketing than operations and support in terms of the value they bring to the company. Operations and support is seen as similar to facilities. In terms of the value that they bring to the company. There is a lot of resentment against ops and support in general from companies. They see it as an over priced expense and have had bad experiences in the past with poorly implemented systems. Similar to some artisan professions might experience i guess.