Very good points and a excellent postThat isn't all possible generational applications. Why do you assume that the word "generation" can only refer to people who live during a certain time period (usually of around 40 years or so)? Do you not know that the word (Greek: genea) has other definitions besides that? Look at this verse:
Matt 12:38 Then certain of the scribes and of the Pharisees answered, saying, Master, we would see a sign from thee. 39But he answered and said unto them, An evil and adulterous generation seeketh after a sign; and there shall no sign be given to it, but the sign of the prophet Jonas: 40For as Jonas was three days and three nights in the whale's belly; so shall the Son of man be three days and three nights in the heart of the earth. 41The men of Nineveh shall rise in judgment with this generation, and shall condemn it: because they repented at the preaching of Jonas; and, behold, a greater than Jonas is here.
Notice that Jesus compared "this generation" to "the men of Nineveh". He was not comparing two time periods, He was comparing two people groups: believing Ninevites and unbelieving Jews. So, in that passage "this generation" was not a reference to people living only in that particular time period but was a reference to unbelieving Jews.
I believe every time Jesus said "this generation" He was not speaking of a particular time period but of the unbelieving Jewish people in general. You asked about Matt 23:36. Let's look at the verse in context.
Matt 23:33 Ye serpents, ye generation of vipers, how can ye escape the damnation of hell? 34Wherefore, behold, I send unto you prophets, and wise men, and scribes: and some of them ye shall kill and crucify; and some of them shall ye scourge in your synagogues, and persecute them from city to city: 35That upon you may come all the righteous blood shed upon the earth, from the blood of righteous Abel unto the blood of Zacharias son of Barachias, whom ye slew between the temple and the altar. 36Verily I say unto you, All these things shall come upon this generation. 37O Jerusalem, Jerusalem, thou that killest the prophets, and stonest them which are sent unto thee, how often would I have gathered thy children together, even as a hen gathereth her chickens under her wings, and ye would not!
Notice that He speaks of "this generation" as being those who He would send "unto you prophets, and wise men, and scribes: and some of them ye shall kill and crucify". Then He speaks of "Jerusalem, thou that killest the prophets". So, He was directly associating "this generation" with "Jerusalem" or more specifically Jewish unbelievers who killed the prophets. But it wasn't just the Jews of that time period who killed the prophets of God. Their descendants also killed the prophets so Jesus was referring to a type of people and not just to those who are alive at that time.
Notice that Jesus referred to them as a "generation of vipers". He was not identifying them by the time period in which they were living, He was identifying them by their wickedness. Notice He was even holding them responsible for "the blood of righteous Abel". The Jews living then obviously didn't kill Abel so that means He was referring to a type of people (who were like Cain - wicked) rather than just people who were alive during a certain period of time. That can be seen from the passage in Matthew 12 as well. He contrasted "this generation" with the Ninevites. He was not contrasting chronological generations there, He was contrasting two different types of people with "this generation" being unbelieving Jews and the other type of people being believing Ninevites.
The context of Christ's use of the phrase "this generation" just does not support the idea that He was referring to a chronological generation rather than to a certain type of people. He said He didn't know the day or hour of His coming (Matt 24:36, Matt 25:13), so how could He have known that His coming would occur and "this generation" would pass away within about 40 years? I don't think that makes sense. I believe He was saying that "this generation" would not pass away until His coming occurred at the end of the age, whenever that might be (He didn't know). So, for all He knew His coming and "this generation" passing away wouldn't occur for thousands of years. All He knew is that the things He talked about, particularly in relation to His coming, would have to occur first before "this generation" would pass away.