It will always be a problem. GOG tries to make it more painless but you will always find something that is not perfect.
The source of the problem: PC gaming was never hassle free on all PC configurstions at the time of a game's release, so it's hard to imagine this will change in later years...

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qed

Agreed, GOG games usually always need some sort of tweaking. The community is fantastic, but it's not how it should be.

That's one reason why I encourage building a retro PC. Sure it costs time and money, but you spend just as much time crawling through forums to find a solution or fix.

There are games that are major broken, yet they are still being sold. For example Incoming on Nvidia cards or Tomb Raider II.

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Don't know, I'm into building retro PCs 😀

As I wrote, PC gaming was never hassle free. Using a VM will only introduce more hassle. For Dos games, the VMs do not provide as much compatibility as Dosbox. For classic Windows games that don't need 3D accelaration a VM might work. For those that need 3D you will have to install Windows XP in the VMs (as graphics accelaration is typically only provided to VMs with Windows XP due to needed drivers) which adds another layer of problems to earlier 3D Windows games... And so on...

Even if you emulate a period accurate PC or have one you'll still run into quite a few problems here and there. Even if you give up on classic gaming and just play modern PC games then guess what: they have the same problem.

PC gaming was never for people who just wanted to insert a disc and play. That said, if you want it to be easier you could help make it easier. There's a PC Gaming Wiki. If it's lacking information for a game you know needs it, contribute! If you're a bit technical maybe even write installer scripts to install games and automatically perform needed fixes.

It'll never be hassle-free. Funny that someone mentions Gabriel Knight 3, that game is a pain in the ass. I've been slowly playing the GK games since October and as soon as I reached GK3, the trouble began. The game will not properly on modern PCs, even with the GoG version. There are frequent crashes and performance is subpar. I imagine it might be alright under Windows XP or even 7, the biggest issue with performance is that it seems to drop to single digits as soon as some text is displayed anywhere on the screen.

I eventually ended up settling with my Tualatin 1.4 and FX 5700 and the game still runs choppy from time to time (especially once more than 3-4 characters are on-screen). Very temperamental!

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While some blame may lie with Windows, it is too easy and wrong to blame it fully. Big part of the problem is that a PC can be so much different to the next one. Several kinds of graphcis and sound cards, many other input devices, many different drivers etc.
MS recognized the problem and it is one of the reasons for Direct X.
Another big problem is sloppy code and the understandable problem that games are not getting fixed years later for a new Windows version...

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Repeat after me: Working code is not bugfree code.

You can fear all you will, but why really bother before it is really a problem? And you CAN run emulators on ARM...

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Abysmal wrote:

[snip]
I'm guessing these methods won't allow for EAX though, which is disappointing. Still, clicking "install" and then immediately running the game afterwards sure beats the modern alternative.

As far as Wineskin is concerned, some community members of The Porting Team have taken the liberty of creating Wineskin engines using the latest releases of Wine-Staging, a version of Wine officially used to test bleeding-edge Wine features before they're formally added to regular Wine. Conveniently, Wine-Staging has had software support for EAX 1 since version 1.7.40. Yes, it's extremely basic support as far as the complete spectrum of EAX versions goes, but it's better than nothing.

Abysmal wrote:

One of the points I was trying to get at is that Windows is the only platform where each game is fixed individually using messy bandaid solutions rather than creating an underlying core or layer to emulate the entire shebang in one go. While I understand the technical reasons behind why it'll probably never happen, it still feels rather unfortunate. I guess Windows being such a gigantic frankenstein of a mess mirrors the experience of running software on it.

From what I read yeah, the Win32 API's so chock-full of legacy/compatibility code that the developers made it into quite a monster of an API.

In practice it is hit-and-miss, some due to Windows, while others due to how shoddily coded it is, or in the case of Splinter Cell and NFS ProStreet, hardware issues.

This is why I prefer retro machines for DOS games and Windows games for the Windows 95-98 era. You only have one set of hassles to overcome. With GOG or Steam or some other modern packaging, it can add another layer of complexity, especially as modern machines evolve.

For Tomb Raider, my Windows 98 machine can play every one of them, just install the main game, the expansion pack and apply a patch (if necessary). My graphics (Voodoo 3) and sound (Aureal Vortex 2) hardware has solid compatibility with games from the Windows 95-98 era and late DOS games. Slap an ISA Sound Blaster in there and you are pretty much all set outside the slowdown issue.