No, Mark, he is reading the regulation in pure form, or nomal english as he says; which is WITHOUT the understanding that these words in aviation regulatory language have a special meaning. If you understand that the endorsements apply to the aircraft as certified, then the words "retractable landing gear" have a different meaning.
I'm just screwing around with this but I don't think that this involves some hidden regulatory meaning.
The normal English words are
"an airplane that has a retractable landing gear..."
Let's change it to
"a person that has glasses..."
If I'm wearing glasses that are broken or with the lenses covered with tape to black them out, I'm wearing broken glasses or glasses covered with tape; I'm not suddenly not wearing glasses at all.
I guess the "confusion"
is whether
"retractable landing gear..."
means
(1) landing gear, of whatever design, that is capable of being retracted right now (like the disabled gear in the OP's post or a 182 after a =very= hard landing)
;
(2) a landing gear system that is designed for retraction
Me, just on normal English, I'd go with (2). I'd bet that if you ran the question on a non-aviation board, that's the answer you'd get.
There's plenty of "terms of art" and Regulese in aviation, both in and out of the FAR, but I really don't think this is one of the examples.