Were Chazal concerned with "hsitorical sense" in derash?

One comment to the previous posts raised the possibility that Chazal were not concerned with "historical sense". I don’t think that’s quite true and would like to focus on a sugya daf yomi learners may remember from a few weeks ago to make my case. The shakla v’terya: In Kesubos 10b the gemara suggests the term “almanah” is derived from the “manah” an almanah receives in her kesubah. Asks the gemara: the Torah’s use of the word “almanah” long predates the valuation of a kesubah as a manah – the term cannot possibly derive from a takanah which does not occur until hundreds of years later.

Two few points:
1) The gemara’s question shows an awareness of anachronistic reading.
2) I get the impression that some would dismiss all anachronistic reading as derash, and somehow that label renders all questions become moot. I do not understand that approach. The gemara’s reading can’t be pshat – the word “almanah” must have had some meaning to readers of the Torah before the takanah of 100 manah for an almanah was instituted (as the Rishonim on the sugya point out). Yet, despite it being derash, the gemara is still not willing to dismiss the anachronism.
3) Is this sugya an anamoly? We don't find this type of question raised elsewhere to the best of my knowledge. What to make of that - I don't know. I'm just raising the question.