the question would have been brought before the Acharonim and it is entirely possible that the idea of a Jew being able to escape liability for his/her debts/damages would have been laughed out of the beit midrash.
Why on earth would you assume that? If that were the case, there would be no reason why contemporary poskim wouldn’t similarly reject the escape from liability afforded by incorporation.
And the assumption that LLCs would be assur is entirely flawed to begin with; if indeed it were not possible for a corporation to escape halachic debt, there are other aspects to corporations; not every entity which does business with a frum corporation would be subject to the psak of a bais din.