With reference to your parable: When a relentlessly demanding diner shows no appreciation of any of the gourmet meals he is served, and only asks for more, it’s understandable if the generous cook who took such painstaking care over their preparation becomes a little exasperated with him.
In section 30, both your “possibilities” are wrong. The prosecution’s position is that Aristogeiton is disqualified from holding office (by virtue of his continuing public indebtedness, for one thing). That’s what makes his having obtained office in the lottery process so dreadful. He obtained it (aor.) while disqualified (perf.). This should be quite clear if you’ve read the speech up to this point.
To revisit 25.12:
ὅσῳ γὰρ ἂν μᾶλλον (ἡμῶν δειξάντων τὴν τούτου πονηρίαν) μηδὲν ὑμεῖς φροντίσητε,
τοσούτῳ μείζων ἡ καθ᾽ ὑμῶν αἰσχύνη γενήσεται.
Somehow you fail to discern that τοσούτῳ μείζων balances ὅσῳ μᾶλλον (each having a comparative), and you wrongly construe μαλλον with the genitive absolute. (Hylander’s “"the more you completely fail to take heed” was a translation of ὅσῳ γὰρ ἂν μᾶλλον μηδὲν ὑμεῖς φροντίσητε. — μηδεν, by the way, is an inner accusative.)
Such misreading is disturbing, especially in light of similar misunderstanding of sentence structure in other threads of yours, e.g. http://discourse.textkit.com/t/grouping-the-genitives-in-longus-3-9-1/16180/1 I won’t repeat what I wrote there, but there’s clearly something about your reading practice that inhibits your ability to articulate sentences correctly. Something that could help you here is Ed. Fraenkel’s Kolon und Satz: Beobachtungen zur Gliederung des antiken Satzes, or more directly study of κῶλα and κόμματα. LSJ gives ancient references for you to follow up on.
There should be no need for you to reply.