As someone who has a Windows 95 OSR2 install that's also being used to house my DOS game library, is where any way to install DOSBOX-based GOG downloads to that image?

I know it's a pretty roundabout way of doing things but I also play this obscure Win3.1 game known as Operation Inner Space so having those extra directories with .exes would be nice

It should be; I'd install the games on your main PC and then use a USB or optical media to transfer on to your Windows 95 machine. I think most of the "disk based" games should give you all the files you need - for CD based ones, you might need to find the CD image and extract and write it to media. Where you might be stuffed is if they've converted redbook audio to MP3 or something like that.

Also, Operation Inner Space is amazing and well deserving of a re-release on modern windows. Although playing with all those directories on a 2TB SSD would be a LONG game.

So if i'm reading this right, the contents of a standard install through the GOG installer should be put in an ISO like

IMGMOUNT C (path to my Windows 95 .img)
IMGMOUNT D (GOG game packed into an ISO) - t iso

And copy things through Windows?

Yeah, it's kind of a hassle to transfer stuff to a DOSBOX-X guest OS but as of right now, I have really no clue on how the transfer of files from host to guest can be made any smoother.

For installing them - I don't know if GOG installers would work directly under Win95 as they are based on InnoSetup which states "Support for every Windows release since 2006", so they may not run under Win95. It's probable you may need to install them under W7-10, and then copy the game folder across / zip them up and use the zip as your "installer".

For playing them - It may depend on the game. For most non-complex games that are fully installed, playing DOSBox games under an old Windows OS version should be as simple as copying the folder over then starting the game's .exe directly (possibly using some settings as laid out in the .conf file). However, some CD-ROM based games only install some files and require access to read the CD-ROM "live" for the game or soundtrack (ie, it's expected stuff like MSCDEX drivers will be present and that you've configured Adlib / SoundBlaster sound cards, etc, which DOSBox handles automatically but you may need to manually configure if you're running them "direct" under Win95).

And some ScummVM compatible games sold by GOG have had their .exe removed and been supplied with a copy of ScummVM and just the data files (as shown on the ScummVM Wiki), so if you don't have an older disc version you can use, then you may have to source those original .exe's "elsewhere" first to be able to run them (even under DOSBox).

Finally, if the only reason you're running Win 95 is to play 16-bit Windows 3.1 (non DOS) games, it's actually possible to install Win 3.1 under DOSBox, then run them under W7-10. See Chip's Challenge screenshot as an example.

Probably more what AB2012 said. I had thought that you were using a "real" Windows 95 PC as well, but sounds like you're using dosbox to run Windows 95. But yes, I think that you need to be in the virtual environment to copy the files in.

Personally, I'd use PCEM rather than DosBox for Windows 3.11 or 95; but if you've got it working well for you, no need to change. In PCEM, it's pretty easy to change images on the fly (and you end up copying most stuff in by making an image and mounting it)

Have you tried using a virtual machine like VirtualBox to run DOS or W95?

I'm not sure if it would provide a better or worse experience for you than running W95 baremetal, but I imagine it would be a lot more convenient if you have modern hardware, and easier than trying to boot DOSBox. VB does support video acceleration.