I know people say memorizing is the best thing to do, but I found that I just couldn't memorize and keep everything straight in my head. While I was taking Ochem, what I would do is write out the mechanisms, time consuming, yes, but after just copying them down a few times, I could remember them quite easily.
Possibly what you could do is to just look at the rxns in Kaplan, go to your textbook and look at the mechanisms. Then talk yourself through the entire thing. So for example for HBr adding to an alkene you would go, The H adds to the carbon with the most H's on it, then the double bond goes away and you have a carbocation. Here you will have a chance of rearrangement. DO I have the most stable carbocation? Yes, okay so then the Br would attach to the carbocation. Or No, so there would be a 1,2 hydride shift or there will be a 1,2 methyl shift.
This method might help you to remember the reaction order and those PESKY little rules about rearrangement and stereochemistry.