What is 500km in American? :P

310.686 miles according to Google. And I am sure it is MORE than 500km. Also, before you say he can buy and download the game himself, let me assure you that will be severely OVERESTIMATING the internet connection in backwater area in this country. So, if I have no time to properly visit him, the only way I can is to send the installers in a flashdrive via snail mail.

You never visit him? :)

Also, there are remote access software for Windows (I think at least Win8, and possibly Win7, comes with one by default) which let you control a remote PC. So in a sense you could do it all from your PC, ie. download and install the game for him, and even uninstall the game later if needed. He just must grant you remote access to his PC. I've tried it occasionally when I've needed to check things on some relatives' PCs long way from me, that they have all the latest Windows updates etc.

But even then, I think even that goes beyond what was probably intended by either GOG or the game publisher when you bought the game. Installing your purchased games to a remote PC 500 km away from you is not maybe anymore about installing it to a PC in your household, even if it is a blood relative to you.

But, as long as you don't break any local laws, I guess you do what your heart tells you. That's what this discussion was about anyway, there are many shades of grey. And the title of this thread is a bit confusing, as "family" to many probably means the household, and not necessarily your siblings and cousins living far away from you, even though they are blood relatives to you.

EDIT: Ok I read that he has a poor internet connection, so that may complicate things a bit, at least depending how big game we are talking about. However, I have used the "remote access" in Windows 8 through pretty lousy internet connections, even.

If you want clear conscience, you could of course buy a gift code for him, and then send a copy of the game in an USB stick to him, and throwing that gift code the /dev/null (in case you don't want to create a personal GOG account for him, that he can't currently access). :)

He visits me much more often than I visit him :-)
Main reason being that I work for a company, and my annual leave is so very limited, while he works by himself, so he can manage his schedule much better than me. I do plan to visit him sometime next month though.

I assume you are talking about TeamViewer and such, and yes it is great, I use it on Linux.

*laugh*
This time you are overestimating the laws in this country :-)