I have not encountered any really difficult problems. Help locations like this one, Google searches and the things included with the distro have been all I have needed.
I use Aptitude to add and remove packages as well as the command line. I run remote from a laptop a lot and I watch a lot of youtubes. I suspect some of my old video cards are not well supported, but I have yet to find any missing features. It appears to me that if Linux ever supported it, Debian still does.
I used to program in Turbo Pascal, K&R c, etc. I am looking forward to get back at it.
I have felt that Ubuntu is a subset of Debian as defined by a commercial venture. The latest Ubuntu failed to install on my machine but Debian did.
There are lots of choices in Linux. You have to work at it to make a bad decision!
The big advantage of Debian for a new user is that it is stable and it is a rolling release distro. The problem will be getting started.
I think that Debian is a good choice for experienced users, but it is not for newbies. It is a toolbox and a fun one if you know what you are doing. Problems newbies might have are with drivers, especially for old or rare equipment that have only proprietary drivers, and the installer is not especially friendly. There might also be problems getting help as most Debian users are commandline and old school and not really patient with newbies.
I would advise that he stick with a more common distribution based on Ubuntu, which has its own set of problems, but it is geared toward new users and has a large community and lots of online help. For older hardware I recommend Xubuntu. For newer hardware I recommend either Ubuntu or Kubuntu depending on need and work style. New users could also opt for Linux Mint, just bearing in mind that it has no tool for upgrading versions.
If the new user is up for a challenge then by all means go Debian.
Roy
-- John Ferrell W8CCW "Kindness is the language the blind can see and the deaf can hear." - Mark Twain
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