1. What part of the country are you in?
2. Outdoor or indoor venue? Makes a difference in amount of power needed and how much low end.
3. Do you intend to buy your songs as well with that $2000? This question can make a HUGE difference in your equipment budget.
4. Do you plan to do beat matching and full on DJ work, or just play some music? I'm not going into the equipment needed for full on DJ work, it can get overwhelming REAL quick.
FYI - Lonman here is the resident expert, but I'll try to do my best until he shows up.
You'll need:
1. Player
2. Mics
3. Mixer
4. Powered Speakers or Amp+Speakers
5. Cables to hook everything up.
6. Media
7. Effects/compressor/maximizer (optional and the mixer may have them on them)
8. TV
9. Stands, Misc.
Ok... let's start buying:
1. Player - RSQ 333 Triple Tray player - $225. When the single tray players are selling for approx $200 shipped it was worth the extra $25 for the 3 tray unit.
2. Mics - Fender P-51 mics - $50 each x 3 - $150. 2 for the ppl singing, 1 to announce with.
Yes, you can buy Shure SM58's at $100 each, but these are study, sound pretty good, and come with cables. Nady and a few others may be an acceptable choice - but I have experience with these.
3. Mixer - Mackie DFX 12 - $239
4. Powered Speakers - I must refer to Lonman out of my own inexperience/knowledge.
Why? This is where things get sticky AND expensive. You can skimp here and on the mixer to do small groups, but you'll be REAL limited in the shows you can do. I spent $805 on a Fender PD-250 for a small show and it worked VERY well for that show. I'm doing larger shows now and am spending another $1800 to upgrade to another mixer (Soundcraft Compact 10 - $240, NO EFFECTS) and powered speakers (still shopping). If you only want to buy once start smart! JBL Eon15 G2's are $700 each, Mackie SRM450's are $750 each, JBL Eon10 G2's are $550 each but will lack the bass response you'll probably want. Going with a smaller powered speaker means sacrificing bottom end or needing to upgrade soon. I don't have any recommendations that will put you at about $1000 for a pair (the price point you're probably looking for with everything else). You 'could' do a Soundcraft Gig Rac 600 and some non-powered speakers which may put you in the right price range - but you'll probably have to upgrade for any groups much larger than 100-150 (since you'll only have 600 watts (2x300)).
5. Cabling - $150. Probably a little high if you get cables with most of the equipment, but it's nice to have a few spares and be flexible.
6. I'd get the Sound Choice Foundations 1 & 2 - $500. You can go with other sets - Sweet Georgia Brown 1-66 - $110, Chartbusters 1-4 - about $500. The Sound Choice Foundations represented over 2/3's of the songs played at my first couple shows and less than half the tracks. They are well worth the money. Note that you still have to come up with the DJ music if you're doing that as well. I use my laptop and my emusic.com subscription to load up on dance, jazz, and other music. Burn to CD or play direct from the laptop.
7. Effects - Built into the Mackie DFX 12 and also the Gig Rac 600. - $0 BTW, the compressor, maximizer, etc. can wait.
8. TV - 13" TV - Wal-Mart $65
9. Misc - Stand for tv/mics - $70, Fender speaker stands - $120, RF covertor/cable to hook up tv - $25, Duct tape (ALWAYS TAPE DOWN THE CORDS) - $5
That's it. Not counting the media, power speakers or mixer you're looking at about $500. Those few items are where you spend the real money. BTW, all prices are either what I paid or the current list prices for the product online.
I wish you all the luck in the world in your new venture and I hope others can make some recommendations on the speaker area.