Your idea sounds cool and I hope you get some good drills to work out.
Drilling specific tough shots is good, but to some extent learning to make weird cuts like the side pocket one you described... that comes from hitting a lot of balls and just playing more. However position drills are great, and if you can get your team to play decent shape they won't need to make as many hero shots.
I was just drilling a few hanger scenarios with a friend. Shape from a hanger is actually pretty challenging, compared to a ball that's a few inches from the pocket. My buddy and I tried to work out the best, safest route when playing shape from a hanger. Something that can't be screwed up.
Here's some of what we came up with, I'm sure there will be some disagreements, but try them yourself and see if you find something you can do more reliably.
http://pool.bz/P/?@2AaUf2BNOD1QMrQ2...QRBx3lRBx2lasI2lYWN2lUWk1lbWj3layt3lVKj2uBGN@
This diagram is four pages (the page switcher's at the bottom right).
1. Say it's important to fall as straight as possible on that side pocket shot. What's the best route? I think a thin cut on the left side of the hanger, with heavy inside english, gets the most predictable results. The ball spins out three rails, and while it's possible to underspin it (so you contact the third rail too low) it's tough to overspin it (i.e. scratch in the side pocket).
In general thin cuts give a nice predictable route, that's important to remember when playing shape from a hanger. How fat you hit it completely changes the position your cue ball takes, and a thin hit will send the ball on nearly the same line every time. Follow also produces more predictable results than draw.
You can do this by hitting the left side of the ball with low left, and going just one rail... or the right side with low right, and going 2 rails. That latter one isn't bad. But if you practice both the follow and draw options, I bet you find follow + thin hit gives the most consistent results.
2. You have ball in hand shooting the 1 ball to get on the 2. A lot of players do this wrong IMO. They set the cue ball a foot or two away, then try to hit with just the right amount of draw to go into the rail at a flat angle, and then bounce out a little.
The problem is... sometimes the draw doesn't take in time, or the object ball is cut too thin... so the cue ball hits the rail before the draw has a chance to catch. Guess what happens when the CB goes straight into the rail while backspinning? It rips off the rail and travels several feet away (See cue ball B). Another common issue is the soft draw takes better than expected, the player never touches the rail, but instead drifts straight up. That's fine if the next ball is on the rail, but if it's off the rail a bit you end up with a back cut, which nobody loves (See red dot cue ball).
Cue Ball A shows the right play. If you set the CB very close to the object ball, so that you're cutting it backwards a bit, you'll be in a situation where a near-centerball hit is ALREADY travelling upwards towards the object ball. Then you just help it a little with a touch of running english.
It's better whenever possible to cut balls at an angle so that the cue ball travels the direction you want with minimal/no english.
3. You have a bunch of options here, and if the 2 ball can go in either pocket, the simplest shot looks like just hitting the right side of the 1, kinda thin, and going straight up the table. The problem with that is... at a long distance it's hard to control how fat you hit the 1, and the line the cue ball takes afterwards can be a bit unpredictable as a result. It might run towards the side. It might run towards the corner. On a very thin hit it might go straight up the table and land right next to the 2.
The number one goal here (besides position) is to not scratch. I find the safest path is the one drawn. You never come anywhere near either the sides or the corners. The hit is fullish (like a half ball hit or a little fuller) with tons of right spin. It sort of follows the same principle in shot 1. It's hard to overspin this ball, the cue ball should always land somewhere above the left-hand side pocket, when it hits the third rail. This route also seems to leave you a nice angle on the next ball, with little danger of falling straight in.
4. Another idea, when the angle is slightly different the first shot becomes harder (try it). Then this other option makes sense. You hit the rail first, clipping the object ball and then sending the cue ball 3 more rails on more or less the same path as in diagram 3. By going rail first you can 'back cut' the hanger and send the cue ball off to the right. The path the cue ball takes is hugely affected by how thinly you can cut in the hanger. See if you can judge a railfirst shot accurately enough to control whether you hit thinly or more full. A full hit will tend to cause the cue ball to lose most of its speed and die down there.
There are others but I gotta go shoot pool!