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Answer: The practical elements of lifnei iver are very difficult to apply and, if not applied wisely, could make interaction with not fully observant Jews untenable. Your questions, and our response, address the fundamental basis rather than the practicality; we seek perspective rather than a ruling.
You are correct that while most aveirot are violated at a given time, lifnei iver often includes a serious break, timewise and logically, between Reuven’s involvement and Shimon’s sin. For example, if Reuven sells non-kosher food to Shimon, hours or days may go by before Shimon does the aveira. This is not unprecedented. Some melachot of Shabbat (e.g., cooking, planting) consist of doing an action which brings a result only later. Based on this comparison, it is logical that lifnei iver is violated immediately. Possibly Shimon’s violation is a condition for Reuven’s retroactive lifnei iver, or perhaps even if Shimon did not sin, Reuven sinned by "placing the obstacle" as the pasuk (Vayikra 19:14) seems to describe.
Shabbat and lifnei iver are different in that Shabbat is violated without the intervention of another person, whereas lifnei iver requires a person to perform the transgression, usually knowingly. Considering the concept of ein shaliach l’dvar aveira (=eslda; one is not culpable for the sin he had his agent do – Bava Metzia 10b), it would be surprising if Reuven is responsible for what Shimon did, thus indicating that Reuven’s sin was the placing of the obstacle. (One answer is that eslda precludes Reuven’s responsibility for the specific sin, but that Shimon’s violation is the culmination of lifnei iver.)
When lifnei iver applies is difficult to define. The baraita (Avoda Zara 6a) says that one must not give wine to a nazir, but this is oversimplified. After all, it is fine to sell a responsible nazir wine; he can bring it home for his family! This characteristic makes it logical that the violation is that if the sin is done, we apportion blame to those responsible (like when one is careless with his ox, which then kills someone).
Bemare Habazak - Rabbis Questions (657)
Rabbi Daniel Mann
609 - Ask the Rabbi: Beracha upon Returning Tzitzit
610 - Ask the Rabbi: Fundamental Questions about Lifnei Iver
611 - Ask the Rabbi: Amen on a Non-Beracha
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Concerning punishment, no one claims that Reuven receives beit din’s full punishment for Shimon’s sin. However, some sources (such as Rashi, Bamidbar 30:16) refer to Reuven being morally liable for Shimon’s specific sin. There is discussion of whether one can be chayav malkot for lifnei iver (see Metivta, Avoda Zara, Iyunim p. 5), but that does not depend on the specific sin. In fact, most assume (see S’dei Chemed V, p. 341) that one can violate Torah-level lifnei iver for facilitating a Rabbinic prohibition, implying that lifnei iver is independent of the specific aveira, which goes well with the Yad Malachi’s approach.
It seems logical to me that an element of lifnei iver is violated at the act of facilitating, but that it is exacerbated when Shimon does the aveira and by its severity. This also fits well with many sources (further development is unfeasible here).
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