Not defending legalistic bullshit et al. However, at the risk of being the messenger that gets shot I doubt your proposal would achieve anything except (misleadingly) making a bunch of geeks think they'd outsmarted some lawyers. If they cared at all, they'd as likely be amused that the alleged "mockery" missed the entire point- The Law Does Not Work How Geeks Think It Does.
There seems to be a fallacy among some geek types (#) that the law is a fixed set of rules that can be tied down and gamed by exploiting them with some (often borderline ludicrous) interpretation. (##)
It doesn't really work like this- in common law-based countries such as the United States and most of the United Kingdom at least. (###) Even less so when trademarks are involved, which are inevitably dependent upon context and interpretation.
So I doubt you're going to be able to pin down the "cutoff" point because there won't be one. It'll probably vary depending on context and what it's in the lawyer's interest to successfully argue.
And even if you think such tactics are hypocritical bullshit- and I'm not necessarily disagreeing with that- you think the lawyers are likely to be bothered by any attempt to mock them on that basis? Much of what lawyers do- particularly in areas like this- is to find and exploit ambiguity and subtlety in the law in their clients' interest.
(#) As prone as anyone to assuming the rest of the world works in the same way as it does in their mindset and area of expertise.
(##) In their fantasy version of the law, this would typically force the judge to grant them victory because they'd- in their own mind- logically followed that (supposedly) fixed set of rules. In reality, it would more likely see them censured for playing silly buggers and quickly losing the case.
(##) England, Wales and Northern Ireland use common law. The Scottish legal system is a mixture of common and civil law, but I doubt Scottish law would be involved at all with this case against a company based in England.