I'd suspect that this is not so much amelioration as a broadening, so a 'ridiculous amount of money' is a comment on the situation rather than on the amount of money being referred to per se. It would be unusual to speak of there being a 'ridiculous amount of money' in say Fort Knox. It would be more usual to speak of a 'ridiculous amount of money' being taken from taxes to enable a sporting event, or spending a 'ridiculous amount of money' on hair products, or sellers of 'Big Issue' making a 'ridiculous amount of money'. 'Ridiculous' or 'ridiculously' in 'ridiculously large' are comments on the decisions, or situations judged crazy, rather than merely the largeness of the wad of banknotes. So AHD's definition
ridiculous: adj. Deserving or inspiring ridicule; absurd,
preposterous, or silly.
still applies, though at a distance.
Of the following synonyms given at your reference, only some have made the leap to being regularly used to comment on the situation while appearing to modify a noun specifying only part of that situation (eg absurd, ludicrous):
cockamamy (or cockamamie), comical, derisive, derisory, farcical,
laughable, pathetic, preposterous, risible, silly //Related Words
asinine, brainless, dumb, fatuous, foolish, half-baked, half-witted,
harebrained, idiotic (also idiotical), imbecile (or imbecilic), inane,
jerky, moronic, nonsensical, simpleminded, stupid, unwise,
weak-minded, witless; balmy, cockeyed, crazy, cuckoo, daffy, daft,
dotty, insane, kooky (also kookie), loony (also looney), lunatic, mad,
nutty, screwball, senseless, wacky (also whacky); fantastic (also
fantastical), far-fetched, inconceivable, incredible, unbelievable,
unreal, unrealistic, unreasonable; illogical, irrational
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