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Speaking of, did you have anything in mind for that already?

Micro USB seems like the go-to charging connector for this type of thing. However, my searches for panel mount Micro USB connectors in the past have shown they're always expensive (~$10 a piece) and physically bulky. It might be simpler to use a PCB mount connector (either on a breakout or built into the LiPo charging board).

Or you could use a different type of connector entirely. That's an option.

That's really not a bad idea. Shoulder buttons could end up pretty awkward without careful planning, and might need off-board switches. Charging and link ports would probably need to be relocated (good excuse for a proper headphone jack while you're at it). I really wish I had the technical skills to help with a project like this.

I'm not an expert, but maybe a product like this would help? Also, unless you quite literally have no ground (like, no dirt underneath your house), you can hook a wire to a buried water pipe or drive a metal stake into the soil to provide an electrical ground.

As Knife Crimes said, there are some nice little self-contained coils with all of the electronics built in for USB output, designed to sit on the back of a smartphone underneath a case. Example.

I think one of those would connect directly to a USB LiPo charger without issue.

You'll have to make sure that the Game Boy can handle up to 4.2v if you're connecting it directly to the battery. That's about the voltage you'll get during charging and for a short time after a full charge with LiPos. The guide you linked does this seemingly without issue, so take that however you will. If you find the Game Boy can't handle this, you'll need a regulator of some sort.

Also, make sure your LiPo has a built in protection board. Almost all of them do, depends on where you buy it though. If it didn't have that protection circuitry, you could accidentally discharge the battery so far it would be ruined. It also usually provides over-current protection, which is nice if you don't want your Game Boy to literally explode in your pocket in the event of a short circuit.

I think you can get far more accurate time synchronization via GPS or CDMA connections (both can be done via smartphone, for example), but that wouldn't solve the problem. The issue isn't with time synchronization, it's simply with the internet latency between the two gameboys.

If LSDJ was modified specifically to support this and compensate for latency, maybe it could be done.

Awesome! I really need to get around to re-doing my crappy old SP-frontlit Color someday. What subreddit are you talking about?