1. Charts. When planning a cross country, it is necessary to draw nice thick black lines on them to show the route.
Only a readable line is required. And as charts are not that cheap, one that can be erased without ruining the chart. A soft pencil, 2B to 4B should do the job and a quality plastic eraser (don't forget a spare). As for laminated charts, I used to swear by these until I saw the light. A simple hand drawn pencil line does trick and it's a lot less faff. I also saw that the chart can be used for making notes and doing calculations.
2. Same question on the E6-B wind side. It's necessary to draw a line and a point on the face of the wind computer...over time it will just fill up with lines.
Lick your finger, give it a wipe and the pencil comes off. They last for years. But could I recommend that not only do you do the sums with the E6-B, but you also do the drift calculations in your head. I reality, they'll be as accurate but no equipment required and it will be a lot faster.
3. VFR training videos in my King School's Cessna program all show the King's flying over western terrain with *very* obvious landmarks...lakes, rivers, mountains, towns in the middle of nowhere, etc. Where I live, it's all suburban. Everywhere you look are houses, more houses, towns, and more towns. The landmarks are not NEARLY as obvious as they are in the King videos and quite honestly they really make it look a lot easier than it really is in an area like mine where finding a landmark is sometimes like finding a needle in a bucket of needles. Does anybody else fly over what you consider somewhat difficult VFR territory?
I've flown across the middle of Australia (VFR) several times. Charts from the this area look more like an even brown carpet. Virtually featureless, until you look a bit closer. What you are looking for are the exceptions. So if you are looking at a sea of houses, you might like to use road patterns, airports, rivers but don't forget, you don't have to just look down. Look several miles out to the side and ahead and look for the BIG features.
4. GPS or not...I understand that I MUST learn to navigate by pilotage, both for safety reasons in the case of equipment failure and for my check-ride, and because it's just fun (when you can find your landmark!).
Honestly, you don't need a GPS. I'd invest the money saved on a personal beer rental scheme. Or even maybe some good sunglasses (Serengeti Drivers?) or maybe a good headset. But just what will the GPS bring to the party? You are going to have to use a chart anyway to plan with the GPS so just spend a few minutes more and complete the job. And I'll guarantee that I would be able to plan a trip with reasonable ETA's, fuel planning, track planning before the GPS chappy has got the numbers punched in and checked.
5. Autopilot coupled to GPS...a question I've wondered for a while.
It depends on the GPS/Autopilot system. Some are very clever and some are dumb. But even the dumb ones follow the magenta line with such accuracy that you regularly pass over/under each others cockpit - separated by 1,000' feet. Also, in most flight phases the autopilot makes constant minute adjustments so large control inputs will not be required. As for the systems fitted to GA aircraft, I can't comment.
Enjoy the learning,
PM