Reply to Semi-Pro (hahaha) DJ Seeking Your Input

Hey there!
Thanks for taking the time to read this. **If you're short on time, please skip to Questions** My name is Michael, and I'd like to start making the transition into the club scene this winter. I've been spinning for about 2 and half years now, and producing for a year as well. I live in Chattanooga, TN, which is 2 hours in between Nashville and Atlanta. I've been practicing at least 3 times a week since I was 15, and have played out 15-20 times at different private events/parties (to give you an idea of my live experience). *TO CLARIFY* Although I am young, I'm not an idiot. I actually got into DJ ing after buying DJ hero (haha not even kidding). I say that to tell you my motives: I love music, I love to dance, and I love to help people relax/have a good time. Haha, so now that that's out of the way, lets get down to business. I'm currently using a Vestax Vci-300, Vfx-1, and Serato Itch. The only major flaw of this controller is its low output compared to other controllers. I'm turning 18 December 9th.

My Questions:
1. Should I continue using this controller or upgrade to an s2 or s4?
2. Should I join a record pool? I love crate digging to find those free legal gems that me and 5,000 other people may know about; however, do they work? Or should I play mainstream until I get some steam to brand my own sound? (even though I may not enjoy that type of music)
3. Do you club DJ's enjoy your sets? I've seen deadmau5, kaskade, boombox, zedd, excision, fareoh, le castle vania, stephan jacobs, noisia, doctor p, madeon, wolfgang gartner, and eric prydz live. Now I know there's a huge difference between club sets and festival/show sets, but are they fun?

Thanks again for your advice!

Feel free to post links to your originals/remixes/mixes!