I tried to find something more efficient from imerge, but I got the feeling that git is not really intended to resolve merges that are as divergent as this, so I assumed there was no easier way. (Might be that a new tool for this has popped up in the last year or two, though!)

As for merges, generally I want PS+ to be a subset of PS where-ever possible, which means that everything from PS should be kept as far as is reasonably possible.

Documentation: Merge, keep both the PS and PS+ bits.
Demos: Merge, keep both the PS and PS+ bits.
Gallery: I've overwritten the games_dat file for a PS+ specific gallery. So you should use the games_dat file from PS+. I'm still keeping the images from the old gallery, so you can just leave them (or move them to the correct folder).
You should be able to use testdata.js from vanilla PS. Some tests will break because of capitalization changes, you should be able to identify these easily and fix the capitalization in the test data (see Clean up test cases #31 for more info on this). Any PS+ tests are in a different file and should not be affected.
Some files will pop up as added/removed because all folders used to be in the top level folder, before all being moved to the src/ folder in PS v1.7. It's annoying but I haven't found a way to fix it.
JS and CSS will be tricky because sometimes Stephen and I make different decisions. For now refrain from changing anything that isn't a pure merge. If this is not possible, please note which decision and changes you made.

I'd recommend to use imerge and then merge not the entire branch at once, but pick a commit like around ten commits upstream (ideally one you know that's stable, such as a bugfix or vanilla PS release), then test it in the browser once the imerge is completed. This should help you safely merge the thing while still being able to test it regularly.

Please work towards merging the vanilla PS releases and make PRs for each of those once you reach them. Or if you get stumped somewhere, submit your progress up to that point as a PR. This will also help me validate if the merge was performed correctly. See #23 for a good first release to merge towards.

There are instructions in the readme for how to contribute to PS+ if you already have a fork of vanilla PS. 😄

Get latest changes from Increpare #23

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