First, welcome to RCU and to your re-entry to the hobby. I'll try to answer your questions as best I can and answer the questions you didn't ask too.

First, you don't have experience. You never completed a flight on the plane you had before (understandable) so you don't have piloting experience that you can apply to a new plane. You learned a few things not to do, but that's not the same as knowing what you should do.

Second, the good quality brands are worth the money, especially for a guy your age who doesn't have a whole shop full of dad's odds and ends to fix things with. I'm going to direct you back to the Super Cub because it really is a decent flyer that bounces well. You're first plane (and that is how you should think of it) is going to get banged up anyway, so you should pick one that can take it.

Third, do whatever it takes to work with an instructor. If you go to www.modelaircraft.org there is a club locator on the front page. You could probably pull off learning just fine with the Apprentice if you get with an instructor, but I have yet to work with a student pilot on a 4 channel plane that is able to make a 180 degree turn on the first try without me having to take control back to keep the plane from crashing. It's not likely you are any different, so get some help.

On the simulator question, they certainly do help. They don't replace an instructor who will teach you to fly properly, but they do let you practice and develop your orientation and reactions in a no risk environment. Since money is a concern, look in the RCU and RcGroups classifieds to find an older version of one of the popular sims like Real Flight. I only paid $100 for my RF 5 and that was when it was the current version.

On transmitter brands, all 2.4ghz radios will only work with their own brand. So if you buy a Tactic radio, you have to use Tactic receivers or buy the "TxR" planes that Tower sells to go with the Tactic radios. Spektrum works only with Spektrum and Spektrum clones (usually) and the "Bind and Fly" planes that are so popular now.

Now I'll ask a couple of questions.
-What is your flying area like? You'll need more space than you think you do, as you probably learned when you put your old plane into a tree. Basically, if you can see trees in your flying area at all you'll need to make a conscious effort not to hit them.
-Is your dad or another adult going to do any of this with you? Investing in better equipment can make a lot of sense when you are doing it together. And while we're on the topic, what do you parents think about RC planes?
-What is your budget realistically, and how do you hope to progress in the hobby? The reason I ask is that if you'll still have some income to devote to this during the school year and you plan to fly higher performing planes when you're ready, I'm going to suggest getting a better radio like the Dx6i. But if you aren't, you may have to live with a basic 4 channel set for now in order to be able to get started.