(See the best response by Ter13.)
Problem description:
I figured I'd ask, I'm starting to run really dang close to the memory limit... Would making the program Large Address Aware raise my maximum working memory, or would it just break everything once I hit the 2gb cap?
Best response
I don't know of anyone that's tried it. Expect awful results, but I'd be interested in your findings.

Realistically though, there are very few applications you should be authoring in BYOND that ought to approach that memory limit. My advice would be to take a good hard look at some of the patterns you are using and start trimming the fat.

I've never seen a game in DM running close to running out of memory that wasn't using some real asinine methodology in their codebase that could be done better, or just straight up having memory leaks and oodles of junk data because the code is bad.

SS13 gets a pass for being the weirdest clusterfuck of thousands of hours of extreme hivemind volleyball on the internet.
You guessed right on that last one there. Current server I'm on has something closer to thousands of light sources as "a global solution to sunlight" on the highest accessible Z. Which is dumb. But I guess it never hurts to try?

I'll return back with my results.
It works! It works just fine. No negatives known! Using a Large Addreess Aware mod, one can raise the maximum memory before crashing from 1.85gb to 3.3gb! That's really good!

Though 64bit byond would be nice too :^)
Can I bother you for a moment of your time to post something in Tutorials & Snippets?

Like a rundown of the problem, and how you managed to fix it? You know, as a general tutorial for anyone making a BYOND game that wants to do something huge?

The x64 native BYOND build thing is a thing that needs to happen, but people knowing you can avoid the hard crash for using a bit too much memory might be enough assurance for some people to actually, you know, stop despairing and just work.