Does it seem like it's going to be a problem sending me those documents?
Do you think it's going to be difficult for you to get me those documents?
この場合、次のような言い方ができますよ。
ーDoes it seem like it's going to be a problem sending me those documents?
「私のその書類を送るのは無理そうですか?」=「その書類を送ってもらうのは無理そうですか?」
ーDo you think it's going to be difficult for you to get me those documents?
「その書類を私にくれるのは難しいですか?」=「その書類を送ってもらうのは難しいですか?」
ご参考まで!