S. Lewis Johnson's The Old Testament in the New examines precisely those questions via the lens of six particular texts. (I can promise you, it was available for less than $58 when I bought it. Sorry.) This isn't a definitive text on the subject, but it's brief (94 pages), extremely readable (apart from some text comparisons in Greek and Hebrew), and puts some crucial issues on the table. Here's his conclusion:
[The Lord and His apostles] are reliable teachers of biblical doctrine and they are reliable teachers of hermeneutics and exegesis. We not only can reproduce their exegetical methodology, we must if we are to be taught their understanding of Holy Scripture. Their principles, probably taught them by the Lord in his post-resurrection ministry, are not abstruse and difficult. They are simple, plain, and logical. The things they find in the Old Testament are really there, although the Old Testament authors may not have seen them fully.This view is not without objection, but it seems reasonable that it ought to be our starting assumption, at least until compelling evidence to the contrary is produced. The burden of proof lies with those who would argue that Jesus and the Apostles used OT quotations in ways that are incompatible with original authorial intent.
In the final analysis the biblical interpreter is interested not only in what the inspired author meant but also in what God meant. Therefore, the New Testament understanding of the Old Testament is the true exposition of it, because it supplies the reader not simply with what Moses and the prophets understood but also with what the Holy Spirit understood, gave to them, and empowered them to write down. [pg. 94, emphasis original]
P.S. I didn't try to track down all the links, but you may be able to find a better deal here.