The only issue you have in terms of the HEK is with tool; it bounds checks the resulting cache. It is very possible to do, you would just have to modify tool, haloce and haloceded to allocate more memory (among other things).
The only issue is that the "upgraded" maps would crash non "upgraded" games (who are not running OS).
Actually, if you were to investigate the OS code you would know that it is setup to compile for 1.00 and 1.08.
I think anyone not able to cough up like $10 for a legal HaloPC copy is a waste of space on this earth and I don't see why you would want to support them, but thats just me. You can either use a framework to upgrade the game to allow you to use higher content, or continue to want to spoon feed would-be bottom feeders.
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