I find this stuff fascinating, but these books are so dense and have so many cross references.
Ironically, it seems that the best sources of information density are also crazy believers. Maybe finding a former Christian who dissects Revelations and Daniel and so on would be the best option.
I watched this, but it seems too soft and glosses over the inherent violence (with some gentleness) of God as laid down in Revelation. Seems to be a decent first run of getting some of the cross references detailed, but it is from a biased Christian. Yet I also don't want a biased atheist (meaning heavy animus) dissecting it.
Good luck finding something evenhanded that is not too dense or maybe too colored by the politics of the day the commentary was written. Back in Community College (about 1975), there was this "fundamentalist" church near the campus that had tracts that had this super fantastic conspiracy theory. In it, the end days revolved around Cold War politics, in the midst of attempts by the PLO militia to push Israel out of southern Lebanon, which they had occupied some years earlier to prevent rocket attacks from Shite militias that controlled most of the country. The PLO, being Palestinian, which at the time was mainly Sunni, was in a constant battle with the Syrian backed militia, and I think they hoped thereby to improve their chances of causing the collapse of modern Israel (very unlikely).
This fertile soup is what fed the growth of the US Fundamentalist Christian movement of the time. Being relatively new to the whole subject of "end times" interpretation I picked up a book
Understanding Revelation by Gary Cohen (a 1968 monograph based on a ThD dissertation) that talks about Revelation, Daniel chapters 7, 9 & 11, and the "Little Apocalypse" in the gospels of Matthew & Luke. While this helped, it was quite stilted in its language and the author spent a lot of time engaged in apologetics disguised as a serious examination of the subject.
The "historical critical" scholars of the late 19th century could be seen in works by R. H. Charles, but his stuff could plow one over with technical details. Even these were colored by the prejudices of is time. This might be the overly dense stuff you mentioned.
Modern scholarship can also invest a lot of time and effort into analyses which integrate the "Little Apocalypses" of the gospels and Daniel, but many times this too can be thinly disguised modern apologetics (political & religious).
If you want to try to investigate these relationships yourself you'd have to find good translations of the NT (better yet more than one translation), of the OT Hebrew/Aramaic, and the Greek translations of these writings (mainly the Prophets) that Christians preserved (there were two different Greek translations of Daniel). You better also be good at using spreadsheets and/or document tables.
If this seems overwhelming, well, it all is. There were some good discussions over at Peter Kirby's BC&H recently. There is a lot of original language analysis over there, but usually English translations to go along with it. Just read what you can, and ignore what you can't, or make efforts to pick some of it up as you go. It's not rocket science (more like organic chemistry). There will be a lot of bits of data to keep up with, but not beyond the capacity of normal human beings of average intelligence. But most of all, have some fun with it.
DCH