A few years ago, I wrote a post that addresses some of the principles involved in Biblical prophecy and discusses some examples of prophecy fulfillment.
Steve Hays wrote a post on the mechanics of prophecy, addressing issues like why Biblical prophecy isn't more specific.
Here Steve addresses distinctions between different types of prophecy, such as conditional and unconditional predictions.
Here Steve explains that prophets would put their knowledge of the future in terms familiar to them in the context in which they were living.
And he wrote about the reasonableness of gaps of time within prophecies.
Steve also wrote a post about the initial unlikelihood of much of what the Bible predicts.
And here he addressed the dating of the book of Isaiah. I wrote a post on how Isaiah's Suffering Servant prophecy most likely refers to an individual rather than Israel or a group within the nation. The post also argues that the prophecy provides evidence for Christianity even if Jesus' fulfillment were typological. For more about how the passage provides evidence for Christianity, see here.
Here's a thread with links to resources on the dating of the book of Daniel. Most of the links are in the comments section of the thread. And here's a post with links to resources on the historicity of the book. See here on some evidence from Josephus. This post discusses how poorly a Maccabean date for Daniel explains the first half of the book. The post here addresses an inconsistency in an argument against Daniel's traditional date. And the posts here, here, here, here, and here discuss Daniel 11, Antiochus Epiphanes, and the date of Daniel. Steve wrote a response to Craig Blomberg on giving Daniel a late date. Here's a post about how the writings of the Essenes provide some evidence against a late date for Daniel. Another post addresses a problem Daniel 9 poses for theories about a late date for the book. And here's a post about what historical corroboration we should expect for the book of Daniel. I wrote a post reviewing a recent commentary that argues for a late date for the closing chapters of Daniel. In the post, I argue that some of Daniel's prophecies have been fulfilled after the Maccabean era, which means that the book of Daniel is highly evidential for Christianity even if we grant a late date for the book or its closing chapters.
Do passages like Matthew 2:15 dishonestly or mistakenly take the Old Testament out of context when they claim that prophecy has been fulfilled? What should we make of what might be called typological fulfillment? I addressed such issues here.
Sometimes the meaning of a prophecy is disputed. Is an Old Testament passage actually referring to a messianic figure in the distant future? Or is it referring to some figure closer to the time when the document was written? And sometimes the fulfillment of a prophecy is disputed. Was Jesus actually born in Bethlehem, for example? In other cases, both the meaning and the fulfillment are in dispute.
Concerning the meaning of prophecy, Steve has written a post about Isaiah 7:14. I wrote one about Isaiah 9:6-7. Micah 5:2 is addressed here. The posts I've just linked are representative examples. You can find more posts of a similar nature by searching the archives.
We've addressed many examples of prophecy fulfillment. On Jesus' Davidic ancestry, for example, see here and here. Concerning His birth in Bethlehem, see here. On Psalm 22, see here. And here's a post on Jesus' influence on the Gentile world. Steve provided some examples of non-Messianic prophecy fulfillment, and I gave some other examples in the comments section of the thread. Again, these are just several examples among others that could be cited. Any interested reader can search the archives to find more posts about the fulfillment of particular prophecies.
Here's a post by Steve in which he recommends some resources on Messianic prophecy. And here's a post in which he responds to a book by Joseph Fitzmyer on the subject.
I wrote a post that, in part, addresses the contrast between Jesus' fulfillment of prophecy and Muhammad's alleged fulfillments. And here's a post on prophecy fulfillment in general in Christianity and Islam, countering common skeptical suggestions about how easy it would be to duplicate Christianity's prophecies.
Regarding Jesus and the apostles' alleged false predictions that the second coming would occur in their generation, see my post here, written from a futurist perspective. Paul Manata addresses the issue from a partial preterist stance here. In the articles just mentioned, Paul and I link to other posts that are relevant as well. Gene Bridges made some comments on the subject in a post that outlines his view of eschatology. Steve wrote a couple of relevant posts here and here. Concerning the references to nearness of fulfillment in Revelation (e.g., "the things which must soon take place", Revelation 1:1), see here and here. Steve also wrote about how critics' objections to passages like Matthew 10:23, 16:28, and 24:34 are problematic for their late dating of the gospels.
Paul wrote a post arguing against hyper preterism.