I've spent several hours with this dilemma. 3-4 years ago, I purchased Rimworld directly from the developer. So I get the DRM-Free game, and the Steam key.

I have only 5 games in Steam (all of them except Wolfpack, are giveaways), and I'd like to migrate all of them to GOG, but they're not avaliable here. I hate DRM.

Now I want to purchase a Rimworld DLC (maybe two). If I purchase it directly from the dev, I could play Rimworld DRM free (but without autoupdates or cloud saves) or using Steam, which I want to discard.

If I purchase it from GOG, the problem is I need to pay the base game, which is quite expensive, again. But I would have the auto updates and cloud saves, and I would be closer to having GOG as my only gaming service.

Both options make me feel "silly". That's why I ask for your opinion!

(note: I tried to contact Luden studios for ask for a key for GOG, but they say that's impossible)

Look at it this way:
By buying directly from Ludeon you're only helping the game's developer.

By buying from GOG you're helping the developer + a store which sells DRM-free games. I can understand your dilemma because I'm also interested in buying the lastest Rimworld DLCs, but they're still too expensive (I can buy almost a dozen GOG games for the price of Rimworld's last DLC alone).

GoG doesn't Want to provide the ability for developers to generate their own keys.

of course tt would be pure win for GOG, getting more people to use their service which leads to more sales

When I get the option to buy a DRM-free build direct from the developers, this is always my choice. Because that way they get more of my money in the end. I see no reason to feed a third-party when I can avoid it.

Hardly anyone sells directly, so I don't even look for that.
Ubisoft and EA and Rockstar I buy on their platform however.

Apart from that GOG is my favorite, followed by itch, fireflower and so on.

Before I check Steam out, I first go to Epic. Only if nothing else works, I pick steam or don't buy at all.

@OP: you have to decide if having cloud saves and auto-updates and DRM-free all together have enough value to you to be worth the financial cost of double-dipping on the base game again, or not.

Ask yourself which option bothers you more: having those things all together, or double-dipping. Then go with the option that bothers you the least. That would not be a "pure win" for GOG, because that would open up the door for GOG keys to start appearing on grey market websites, which would then compete directly with GOG itself, which would disincentivize GOG customers who are in countries that have the highest prices from actually paying those prices, because instead they could just buy a grey market GOG key that the seller had bought from a low-cost region and then re-sold in a high cost region, but still at a lower cost than the "official" GOG price for that region.

If you have an option to do so then directly from dev of course.

Buying straight from the dev to give them 100% of the profit sounds good on paper but eh... I think GOG (and Steam for that matter) earn their cuts by offering convenience features and library management. I mean maybe 30% is too high (hello Mr. Sweeny) but since GOG supposedly loses money every year you can't claim they're rolling in sweet, sweet developer cash.

I obviously don't know the details of the contracts but I would agree that judging by the state of things, GOG almost certainly gives a fair amount to developers as well.

Thanks for everyone for your replies. I've read them carefully and finally I've decided purchase the DLC from the Ludeon website, and I'll save the vanilla money to purchase another games in GOG. As much as I love GOG, there is no sense into purchasing the game twice if I already have it DRM Free. I may even include it in GOG Galaxy attaching the executable.

Anyway I'd wait few days before purchase - maybe a miracle could happen and GOG may revive it's "GOG Connect" :P

Wolfpack is DRM-free. It's just not here.

Will I get into trouble for telling him where to buy a game that isn't available here? No links, of course. :)

I think you're talking about John Tiller's game (single player) but I'm talking about Usurpator AB game (multiplayer, https://www.wolfpackgame.com/).

My experience from buying direct from Devs hasn't been great

Torchlight dropped their client in favour of Steam Only (it did eventually come to GOG)
And another game whose name eludes me did the same

I think the basic is to buy directly only drm-free games... like those who use humblebundle widget or itch widget on their website or even a basic account/download installer thing.
Don't buy directly from developer if they use a client.