First of all, NOBODY can tell you what the best DJ software for you is. All they can do is say what is THEIR best DJ software. Same goes for organizing your music. If you are set on using Pioneer (club) gear only, then RekordBox is certainly the most logical choice. But if you want some more flexibility, a better bet is using iTunes. Especially since iTunes is integrated in all DJ Software, including RekordBox (the management software) and RekordBox DJ (the full DJ software).
If you start searching these forums for posts on starter controllers, you will find lots of recent discussions on the subject. And you will, probably, notice that we have a pretty standard way of tackling these choices.
It all begins with defining your workflow. And while this is hard if you are not a full-on experienced DJ (yet), you can always work with your intended workflow. The next thing is to find the software at that most closely fits your workflow. Not too long ago that had you picking from three big ones, Traktor, Serato, Virtual DJ and one nearly there, Mixvibes Cross. Today I’d say there are 6 major players: Traktor, Serato, Virtual DJ, DJay Pro (Mac only), RekordBox DJ and Mixvibes Cross. And there is a host of less-known and smaller brands that have offerings.
Once you picked the software of your choice, you should set yourself a budget. As you have already noticed, it’s easy to get hooked by all the shiny knobs and flashing lights and find yourself spending more than you intended and/or than the bank is comfortable with.
Finally you pick 2 or max. 3 controllers (read: setups, but I believe that, unless you want to go full on with NI (Traktor) or Akai (other software) modular controllers, an all-in-one is the most practical) that fit your workflow, your chosen software AND your budget and try to get some hands-on time with them (store/friends/etx). Then you pick and go with it.
Seeing where you stand now, I’d say that picking the right software is your first priority (based on your intended workflow) and then getting a controller. I’d suggest going for a more starter controller. It will still give you more features than the X1 and in a totally different form factor. It will also not break the bank. You won’t need an analogue mixer either. If you are willing to go used, then you can probably find a really good deal.
This will give you all the time to decide if your software and controller choice are correct, get some experience playing out, figure out your workflow in more detail and when the time comes to get your “grown-up :-)” controller, you will have way more relevant (to you) information to make an informed decision that you won’t regret.
Spending more than 500 now for something you don’t really know is right for you could end up a costly mistake.
I can tell you lots about playing out and bringing/hooking up gear, but that is for another post.
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