I actually thought Jackson's book was kinda fun...but then, I like a good challenge. It's really a math textbook in the guise of an E&M textbook. It should generally not be your first exposure to E&M or vector calculus, and as such, it will not have new physics to teach (you should already know Maxwell's equations and some basic stuff about E&M fields). What it teaches are the mathematical methods for dealing with more complex Poisson problems, by relaxing the symmetries used in more elementary works like Griffiths, hopefully to promote a more general understanding of how electromagnetic phenomena can be calculated.
Some important analytical methods are learned, such as spherical harmonic expansions, Bessel function expansions, eigenfunction expansions, and multipole expansions (using both spherical and Cartesian multipoles). Green's method is demonstrated for solving differential equations with a source term, and is applied to Poisson's equation under several different boundary geometries. The book also gets into (multipole) radiation, various geometries for waveguides, and a demonstration of various laws of optics derived from Maxwell's equations in different media; however, these are covered in the second part of the course, which I haven't taken yet.
For most of the problems in the book, there are (at least) two ways of getting the solution: a long, tedious, but obvious way; and a much shorter, elegant, but non-obvious way. It helps a LOT to think about the problem a bit and try to find the more elegant way to do it. In particular, pay attention to results derived from previous problems, because they will often apply to later problems. Also, many problems actually give you the solution, and ask you to show that it is true; therefore, if you get stuck, you can often simply start with the solution given, and show that it satisfies whatever rules it ought to satisfy, thus working the problem backwards. I suspect this is actually how Jackson intended some of the problems to be solved, though I'm not completely sure.
The one thing that will save you the most time on the homework problems is knowing how to manipulate vector quantities, and do vector calculus, without writing out the components. The only problem with this is that, in my experience, schools don't usually teach this enough in prior vector calculus classes, so it requires some independent learning. Knowing how to manipulate expressions with vector derivatives and integrals, without actually computing those derivatives/integrals, will often get you to the solution in fewer steps. In observing the other students in my class work their problems on chalkboards, this is one of the things they wasted the most time on.
And lastly, many of the problems will seem impossible at first glance, or seem not to provide enough information. The key thing is to start actually trying things to get some insight. Also, the biggest error I made in the class that made it difficult to do problems was forgetting to use Maxwell's equations. It seems they should be obvious enough, but there is a strong tendency to try to rely only on vector identities. If you get stuck on a problem, the first thing to do should be to go back to Maxwell's equations; they often supply the piece of information you thought was missing.