Nesting subordinate clauses

Question

I am trying to figure out if nesting subordinates is a reasonable way of stating a double subordinate. To give an example, how should the following sentence be translated:

Could you tell me if there are any news about the documents that I should send.

1. Nested subordinates, treating a subordinate as a determiner of 'die Dokumente', but moving the verb of the outer subordinate (ob es [...] gibt) to the end:

Könnten Sie mir sagen, ob es Neuigkeiten über die Dokumente, die ich schicken muss, gibt.

2. Subordinate after subordinate, which means that 'gibt' won't be sentence-final:

Könnten Sie mir sagen, ob es Neuigkeiten gibt, über die Dokumente die ich schicken muss.

3. Restructuring the sentence to have 'über die Dokumente' determine 'Neuigkeiten' and avoiding the nesting in example #1 (this is the output I got from an online translator, sounds good and doesn't seem to break any grammar rules as far as I can tell):

Könnten Sie mir sagen, ob es Neuigkeiten über die Dokumente gibt, die ich schicken muss.

Answer 1

All of your variants are (mostly) correct and can be used without any problem. Which one to use is a question of style.

(1.) is correct, but the separation between the verb and the clause that it belongs to makes it a bit clumsy and harder to understand than necessary.

(2.) is the most easily understandable solution in spoken language in my opinion, because it conveys the information in the order in which it is needed. The comma belongs after "über die Dokumente" though:

Könnten Sie mir sagen, ob es Neuigkeiten gibt über die Dokumente, die ich schicken muss?

(3.) is also very good, and it's slightly more natural in writing than (2.). If you have a sentence with a longer verb or additional fluff, you might get too much separation between the relative clause and the noun it refers to.