Go to Staples, buy some stick on tabs. Buy the Garrigus X3 Power book, read it, use the tabs to bookmark places you are going to want to refer back to. The Cakewalk manual (pdf) is 2100 pages - it has a tutorial in it - print it - do it.
If you've got 30-40,000 dollars laying around, and you go to recording school, one of the exercises is mixing with headphones. You can't do it. Buy a self-powered speaker that is bi-amped. Go to Recording Revolution website and find the review on cheap monitors.
Don't listen to folks telling you (at this stage of the game) to worry about your room acoustics. There is no end to that trail short of hiring an acoustical architect and rebuilding. If you are curious, download REW5.0 (its free) and analyze your room. It will suck. But it will not suck to the point of affecting what you are doing. I've made decent recordings in the past holed up in a drum booth good enough to get me a record deal.
Recording is an art form. Just like playing guitar or piano. The more you learn the more you will realize you need to learn. You will also realize that you are getting to create something that wasn't there before, and that is a good thing.
As to answer your post (should I upgrade?), isn't that a factor of your financial status? You've got to get some speakers ($120), a descent microphone ($100), mixing board ($250), A/D audio interface ($80), and yes headphones (get Koss ProAAA for $80 or so on Amazon -- don't fall for the hype -- there is very good environmental reason to believe that hearing acuity of people living in 1975 is much better than today and that there's a reason these pro headphones have been around since then -- they sound good, they isolate, they withstand abuse ). The guy who owned the studio I used to work at kept 10's of thousands of dollars in cash in his glove compartment. If that is you, well, why ask the question?