Purely out of curiosity, if someone wanted to purchase every game in the GOG library, would there be some sort of significant bundle pricing? Would that even be allowed? I don't anticipate needing to download every single title instantly, but on a as needed basis, or some reasonable download cap to help prevent redistribution in the event this is allowed.

There's no systematic bundling process for this. Maybe ask GOG support, it's such a unique request that it couldn't hurt.

That's an interesting question. Outside of things like weekend sales, GOG doesn't really do bundles (but they should, at least series bundles). As for buying the whole catalogue 'wholesale', perhaps you could work something out by writing to them.

What we know so far
There is a limit of 50 items per order, whether for yourself or as a gift.
Only some "Scaling Promos" had a "the more you buy, the less per item you pay"
There isn't any kind of cap on how much you can download and how often, I did d/l 260 games or so in 2 days, so I doubt it would be that much of a problem to mass download them.
Speculation
It might be possible to make a deal directly with GOG.com, but for that you'd have to contact them directly.

Right now, no, there's no discounted option for an across the board bundle purchase, or if there is nobody has ever done so. The last Christmas sale however dropped most of the games to half price, and there are sometimes tiered discount promotions that go from 20% to 60% or something similar for certain companies.

I would guess they have some sort of "download safeguard" to avoid the obvious piracy attempt. So if you download the same game 100 times a day they might get suspicous...

The closest thing to that would be the increasing discount model that GOG experimented earlier, ie. the more you buy (or already own) in certain promo, the bigger the discount percentage will be.

Judging by the bitching, most people hated that model (I didn't, even if it meant I ended up buying games I didn't crave so much, just because they would increase the discount). Maybe that's why I don't recall seeing it for some time, nowadays it is the flat promos only.

That said, if you really are into buying all or most of GOG catalogue, waiting for some grazy summer or Christmas sale would be the best bet, as at least earlier most games have been sold on discount then. I got most of my GOG games last Christmas.

With the exception of two indies (one that hasn't been released yet), I have all the games on GOG (though bought over a period of approx two years). 2/3 is probably bought on sale.

What I would like is an easy way to download all of them (not individually one by one). Would it be possible to add an easy batch download function? I haven't downloaded anything in a while though, so it might be that it is already possible.

There were a few downloaders that supported mass downloading, though not sure how many work after the site was redesigned. You should probably check the wiki.
Alternatively, set your shelf in list mode (aka not shelf), and spend about 15-20 minutes adding them to the gog downloader. That's how I did it, took some time but worked.

Great responses I honestly loved the feedback. I think it would be cool to have like a season pass you know, download any game anytime you were thinking about it. Say I want to play Myst and then I find out I want to put it down right away and play something else.

Anyhow, just spitballing

I like this idea.

I just wanted to take this opportunity that THANK every poster in this thread. THANK YOU.

Because now I don't feel so guilty about the amount of GOG games I've bought. :P

My problem as a aging gamer, I have like a 10 minute attention span sometimes, but nothing plays as great as some of these classics.

Aging? LOL, I figured you to be a young 'un by your screen name. I'm old and no way I would remember that screen name. If that's your screen name, I'd hate to think about what the password must be.

I forget my User ID's all the time, and I've only got a few variations of OldFatGuy to remember, and sometimes when I forget my password, I can't remember which email account I used to sign up at the forum so that when I click on "Forget your password" it still takes me an hour to find it. And even then I don't sometimes. Probably double registered in several forums. LOL

EDIT ADDED: Oh DOH!!!!

Now I see it's just TheStormTrooper.

Told you I was old.

I look at my shelf sometimes and wonder how much of my jobseekers vanished into this store >.>