I guess this is just one of many inconsistencies related to inconsistent conveniences. I expect that the recently accepted special case added to the behavior of try? will add some more.
A special case that is convenient in one situation will probably be inconvenient/confusing in some other situation.
And I guess "fixing" the "inconvenient" side of these special cases will have to be done by adding more special cases, ie by counterbalancing rather than removing special cases, since they were introduced for the sake of (local/isolated/case-by-case) convenience/ergonomics. This breaks down the difference between "fixing" and "introducing" bugs.
I'd vote for consistency over convenience, or conveniences that are consistent / does not involve special cases that can be both convenient and inconvenient.
:P :)