I used to collect boxes but I stopped. GOG versions are easy to backup, own forever and install, which is nice. I can't see any argument for boxed versions being more convenient.

I like boxes. Unfortunately, CDs will eventually erode over time. They will do this regardless of how much or how little the disks are read, or how well they're preserved. So if you want to keep your games FOREVER, then you'll probably want to keep making copies of them, and/or keep some disk images as well. Also, someday, we may move away from disks. Currently Blu-Rays can read CDs and DVDs, but it's not unlikely that someday support for all of those formats will be discontinued. Of course at that time you'll also have to worry about whether your game will run at all on a future operating system.

However, with a lot of digital (non-GOG) releases, you're still better off with a disk if the digital version requires activations or somesuch. GoG has a real advantage because of its installers. Even if someday GoG goes out of business, so long as you backed up the installers you can still play the games.

I don't think that you should buy any of those games again unless something goes wrong with your boxed copy, but I also think you should be prepared for the future. It's extremely unlikely that your games are going to last forever, but as long as you keep transferring to the most current format, you should be (relatively) safe.

This is one of the things that I think is unfortunate about computer gaming as an entire system. Unlike, say, a board game or a book, your ability to keep using your games is entirely dependent on how long they remain supported. Unless you feel like keeping all of your old computers in perfect condition, you can't guarantee that you'll be able to pass them on to your grandchildren.

The GOG games are already patched with the DRM cracked or removed. I rebuy most of my physical games on GOG.
When did you have the change of heart? I know you were preferring boxed copies when we were talking about Daggerdale this summer. At some point I just got tired of moving stuff and having it take up space. I don't often get any of them out so what have them hog half my closet?

GOG, because:

1) No box or disc makes for less clutter.

2) No box or disc is better for the environment

3) It allows me to have 2 separate backups that I can re-backup as needed (in my case, access to my games on my GOG account and a separate copy of my games on an external hard drive). No more dependency on a lone copy that you can't backup to play.

4) I can bring my entire game collection with me anytime (an extension of #1) without it implying having to carry boxes of game CDs.

5) Assuming that GOG stays afloat and keeps the games that I got on their catalog, my games get updated with latest patches (no more fishing for them on the internet each time I reinstall my game) and tweaked to work on current OSes so no more compatibility nightmares

6) The price is more affordable than anything you'll find on retail (you can find games as low as 2$ during promos... cheapest I've seen retail go is 10$).

7) When present, the soundtrack is always nice.

I can. When you live in a country with crap broadband. Admittedly for us GOG'ers, most of the classics are small enough it does not matter.

I recently purchased two 1GB sized games on sale from elsewhere, only to find out I cannot pause/resume the downloads(!?) - it'll take about 10 hours to get them each. I wish I got the discs instead now.

I like the paper manuals and maps from my old boxed games. Never giving them up. :) So long as the games work on the newer OS - if not, I'll happily GOG them, and have the best of both worlds. Or, on rare occasions, just to get the other extras like soundtracks.

Both.

I like having the original big boxes visible on my shelves, and GOG makes for no annoying CD swapping.

Definitely both.

...If you can spare the extra coin, that is. But I've seen enough party enhanced empty bottles of beer to know that some moneyz can get spent better than others (specifically in this case, a lot of money is lost for little gain (some sexy action maybe) and in fact a more likely result is a nuclear headache and lots of vomiting).

GOG-like installer, and an external HDD. :p

I prefer physical medium myself. I like the assurance that it's there if/when I need it. Mainly because I have a DSL connection and can't get cable where I live so it takes days to weeks to download multi-gigabyte files. Not to mention if my connection dies for some reason or another I have to start it all over again (which is really maddening at 98% complete).

However for games I have missed out on, never bought, or have ruined physical copies of that are very hard to find original physical copies of, having a digital distribution of it (a la GOG) is a great service and may explain why I have a shelf of 50+ purchased games. No DRM is a plus as well. Although once I have enough games to fill a DVD I burn them to one so I have a physical copy, plus I back them up to my home file server. This way in case I have computer trouble or what have you I always have them if/when I need them.

For me - there is no "better". I would keep both - why?

GOG is good because you are getting your old games without DRM and working on modern PCs. But I would still keep some backup of GOG's games "just in case" (nothing lasts forever, also pressed CD/DVD is much better than recorded one), and I like to collect games so I would not be able to throw away my favorites.

Nice to see both sides of the question. :)
I guess I'll keep them around for a while.

Most my games (if any) has DRM, anyway.

In theory I prefer retail, but it practice I prefer GOG.
"Steam activation required" makes retail copies less important for me nowadays. I use GOG as much as possible, though I will happily buy a retail disc that doesn't require Steam. It's not that I don't have a Steam account; it's that I hate the point of a physical copy being negated by an online activation requirement.

Unless you're a collector, I think nowadays GOG is the better alternative: easier to store, no DRM, no changing of discs, no worries about scratched discs, you can install them on rigs without disc drive (e.g. netbooks), fully patched, Vista & Win7 compatible, you can download them from wherever you are, so no need to take your discs with you when you move or travel.

The retail copies might have a few advantages, too. For example, I'm not sure if the GOG installers would work on older systems like WIn98 (I still own an old Win98 PC, although I admit I hardly use it anymore). And your retail copies might include specific language support that the GOG versions don't offer. But generally I think the GOG versions are superior.

Personally I wouldn't go as far as to buy all the games I already own in retail another time on GOG though, probably also because I seldom ever replay games I finished. I did so with Planescape: Torment, so I could install it on my netbook, but that was an exception because I loved it so much.