Personally I am a very good visual learner. If I see someone do something I can usually replicate it with a fair bit of proficiency. I still have to work on it if I want to master it of course, but physical movement just seems to make sense to me.
As far as developing a strategy, I don't know if I would say that I have a 1 size fit's all strategy when rolling/sparring. Different people will have different reactions/tendencies, so it's more so a matter of figuring out how they react and then going from there. I do have a couple of basic things that I will always fall back on though if need be.
Personally I like to try to find "forks" (if anyone is familiar with chess strategy you know what a fork is) when rolling/sparring. Basically I will do something to my opponent. If they don't react they're screwed, if they do react then I am already waiting for their reaction. Basically it's like setting a trap that they are forced to spring.
Since you like side control, here's one of my favorites from there:
1) use the hand closest to their head to simultaneously fold their nose down upon itself (hope that makes sense) and cover their mouth. We call this "the muffler". It's a great little move because it forces them to react to it; no human being can go without breathing for very long, especially when you are making them carry your weight and they are engaged in a strenuous physical activity like grappling.
You've got to keep pressure into them and kind of cup their face so they can't just move their head and be out of the hold though.
If you want to see an example of it being used, check out Maurice Smith vs. Mark Coleman. My instructors taught it to Maurice and told him to use it against Coleman in their fight, which Maurice did and had success with it. Unfortunately the link's not the whole fight, but if you watch the whole fight you'll see it used.
2) they will probably try to either move their head to shrug your hand off or bridge you to try to force you to base out as their first line of defense. So you've got to have good positioning and like I said keep a hold of their face.
Eventually though they will start to get desperate and will try to use one of their hands to peel your hand off their face. I was taught to control the opponent's far arm with my lower hand (on the bicep) and will sometimes make it difficult for them to use this arm. Whether they're able to muscle their arm out and use it to defend or not doesn't really matter, it's basically just expending more energy on their part either way. The other arm is usually blocked by my body, but sometimes they will manage to use that one.
Regardless of which hand they wind up using to try to peel my hand off I am waiting.
3) if they try to peel with the far hand I will sieze that wrist with my lower arm, then use the hand that had been muffling them to grab their hand by the thumb pad (usually I'll use my thumb as a fulcrum) and twist their wrist (hope this makes sense). I'll then slide my other hand under their arm, grab the back of my own hand and apply an Americana/top wrist lock. I've gotten the lock without the wrist twist before, but really feel that if you can get the twist it's much harder to defend and a much quicker tap.
4) if they try to peel with the near hand I will again seize the wrist with my lower hand, feed the previously "muffling" hand under their arm and behind their neck, and regrab their wrist with the hand that is now under their head. Their arm will now be trapped across their face/neck. This is called a "half cobra" position.
From there I have a few options:
-slide lower arm across their neck and grab my own forearm while simultaneously transitioning to mount to apply a "full cobra" choke. I like this one as most people aren't familiar with it and I feel like it's got a lot of leverage and there is little chance of sacrificing position.
-pop up to knee on stomach/chest and either strike (if it's MMA style) or pull their head towards me while at the same time driving my knee into their solar plexus/bladder to get a tap (sometimes works, sometimes doesn't depending on how "though" they are, fewer people can "stomach" the knee on the bladder though).
-use the half cobra to lever them over, while at the same time driving my lower knee into their side to force them to roll over until I achieve a knee on back/spine position. From there it's any one of numerous submissions that can be applied from a knee on back position (rear naked choke, chin lift, cross face neck crank, etc...)
This sounds complicated, but it's actually very simple and works a surprising amount of time in my experience.