Hi Matt,
I migrated to the SE after using the White's DFX for many years so I'm not exactly in your shoes but I did ponder for many months whether to make the move or not. I haven't regretted getting the SE. Now with that said, I hunt an certain area where another hunts and he uses the Explorer 2 and makes great finds. Also, there are a few folks on this board who have the Explorer 2 ,transitioned to the SE, and decided that the Explorer 2 was as good of a machine as the SE in that there was little or no difference in how the machines work and their ability to make great finds.
Now that I've kind of twisted you up, I think that if I had taken a different path, asked more questions, maybe not gotten convinced that I needed a "new generation of machine" I very well may have sought out and purchased a new, or used but near new Explorer 2 and saved some change. To be brutally honest, if I could afford a backup machine (I gave my DFX to my son) I'd get a Explorer 2 in the drop of a hat.
I guess to summarize, you can't go wrong with the Minelab Explorer, no matter if it's the SE or the Explorer 2.
As for getting in over your head... only you can be the judge of that. Metal detecting and making good finds is a matter of several dependencies such as taking the time to detect, doing research at times, being patient, looking back through old posts on the chat boards for information, and asking questions on the chat boards especially in the beginning. But once you learn your area and your machine you'll have a ton of fun. I know that when I first started out I hit the obvious places like school yards because I knew I could at least dig some clad change; and that I did and it gave me confidence in myself and my machine. I did the exact same thing when I went to the SE, and then I asked a ton of questions. Now with all of this said, you could always start with a lower cost machine and see if you "have the fever", if you don't you're not out $$$. I'm telling you this because over the years I've read tens of "for sale" adds on the boards and eBay where the seller says, "Bought it, used it twice, didn't have the time to put into learning, it's been sitting in the close for a year, the wife's screaming at me to sell it!"
I hope I didn't ramble along too much. If you know you're going to give your all, go for an Explorer. Chocolate? Or vanilla? : )
Take care,
Doug