I’ve done several swaps. I always pull all the staples regardless if I’m reusing the braid or not. Taking the hardware off with the braid kind of keeps everything where it should be making it easyier to move to the new playfield. After you get it moved over you can replace it if it didn’t survive the staple pulling process. Because of this I never have to label any connections. I just take photos for reference and then go to town. I’ve seen people label everything. Kind of a wasted step in my opinion. The key for moving the harness from one playfield to the other is a nice working space. I put the old and new playfields face down on the same work area after all the screws, nuts, bolts and staples have been removed and then just move it over. Works great.

I never met an overlay I liked. That being said, i’m guessing you’re going to need to use your original board a lot for reference points on where to drill on the new board.

That overlay is bad. Are you sure you want to spend the time doing a playfield swap with that? You are talking 40 hours of labor to do the swap. If it isn't a keeper I would just sell it "as is" and include the bad overlay in the sale. Find a different project that will be more satisfying.

Removing the wire harness and hardware is a lot of unscrewing. You want a power driver for that and not a big heavy (and powerful) drill. Handy to put it back together also. Doing it by hand is a pain it the butt.

Swapping a playfield is very satisfying and does make a huge difference in look and play of the game. I just finished a Playboy. I did the cabinet also.

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Sadly this is typical on many overlays.