Right kind of like money laundering 😂
Well it would never really work completely. You could definitely obfuscate with random accounts but for anything of any significant value there are people looking for those transactions, both spam fighters and not so nice people. On Steem the conspicuous thing is the value of posts and transfers, you can't really hide that. It's one of the strengths. So as you say, if not overly large, they might go unnoticed.
However I'm sure that will feel so shady it wouldn't catch on.