Another thing the OP may want to try is to scan local sections of the chart into a computer, and then print out ones most frequently used. If the scan is saved as a bitmap or JPEG, it can also be modified when chart data amendments are published.
Ask, and ye shall receive! In the US, all the VFR charts are already digitized, and are available without charge. Have a look:
Sectional Raster Aeronautical Charts
I bet an iPad is a very useful tool in a cockpit. One strapped on like a knee board would be very cool!
Various "electronic flight bags" (EFB's) are available, and recently approval has been given for the Ipad. Some work better than others, and some pilots have found that quite a few on the market don't do well in unpressurized cockpits; they don't cool as well, and don't last very long. I don't know how that applies to the Ipad.
I use an electronic flight bag, largely because they're permanently mounted in our airplanes. We use them for certain documents, and for approach charts. All our enroute charts are paper.
I've used other EFB's that utilize VFR and IFR charts, though frankly I always prefer paper where I can get it. I should point out that getting FAA approval for us to operate with the EFB's took about three years and thousands of hours of evaluation by hundreds of pilots, as well as the FAA, and that was using already-approved EFB's, and Jeppensen software, updates, and documents. Even so, I make it a practice to have printed copies of the charts I'll be using. (I've had two and three EFB's go dead within minutes of each other, and usually at the wrong time, though not with my current employer. On one occasion, I experienced loss of data because the EFB's failed while approaching Miami, which has about 70 procedures from which to choose, any one of which could be assigned. On that particular occasion, I was in instrument conditions, and couldn't proceed visually to a runway).
Do what works best for you, but always be conservative, and have a backup plan.
I might plot 5 courses on a chart in one night just for practice.
I used to do that as a student. No one ever accused me of being a rocket scientist, so I figured I could use all the help and practice I could find. I'd create tasks or problems, with various wind scenarios, and play out a trip as I did the calculations. When we drove somewhere as a kid, I'd take my E6B and spin it doing times between places, calculating speeds based on my timing, and so on. This is obviously not necessary to do to ride in a car, but still a good exercise in using the wheel. I used my E6B in high school for math, and used the wind side while doing vectors, in Physics. Again, not necessary, perhaps a tad slower, but it kept me in practice.
Martha has that awkward nervous laugh and a really bad hairdo.
Interestingly, I've met them on the road before, when they were out and about in their Citation, and they're the same in person that they are in the videos.
What training system do you happen to like Gupp?
The last ones that I looked at that I thought were good were the plain-jane Sporty's videos.
I'm not a big fan of the videos, anyway, though some people do find that enhanced graphics and a more modern approach works best for them. Personally, I like books. I like to read, I like to write notes in the margins, and highlight and underline and mark up my books. Unfortunately, I'm on the road a lot, working abroad,and I can't carry a huge printed library. I carry a laptop (from which I'm typing this). I have all FAA publications on one disc. All company publications on another. I carry some books (I get overweight bag fees when I travel because my bags are weighed down with books, and I'm fairly sure that my back problems come from hauling all that gear up and down stairs and ramps, and into the airplane each day). To me, it's worth the effort.
Each person's mileage, of course, may vary.