Interesting read this has been. First thing I will say is that as a forum, the whole point is to ask questions and discuss the business. If the only solution being offered is to "Call Ben", then it sort of defeats the purpose of the forum, does't it? I understand Ben is a sponsor on these boards, but there really should be more substance than this thread has shown so far. /end.rant
Now, DJKimber, Welcome, and congrats on jumping into the DJ industry. It's a fun, rewarding industry that can also be extremely profitable if you manage yourself properly.
As for your question, a few suggestions to help you out...
1. Based on what you are looking to do, Powered Speakers are most likely the best way to go. They are typically lightweight, portable, and amount to less hauling and storage space, since you don't need an amp/processing rack.
2. For your software, you mentioned Virtual DJ is a bit expensive. I think you'll find that like most things in life, the better products typically are. There is a reason Virtual DJ has been as successful as they have been, because they have an awesome product. I got lucky and bought it when it was $149. It was the best money I have EVER spent on software. The Free Updates for Life are priceless. Even at $299, it's a bargain. Don't just take my word for it, Numark, PCDJ, and a few others have all looked to Virtual DJ for their own software.
3. There are a number of quality brands that make powered speakers. Yorkville, JBL, RCF, EV, QSC, and, as mentioned, Mackie. Mackie has fallen quality wise since they moved production to China, but they are far from the only game in town. As a DJ, I was always partial to JBL myself, but it's been a few years since I've bought gear for this use, so I don't know what their quality is like now. In my time as a Factory Rep for RCF and the American DJ Group of Companies, many of my Production/Rental House dealers were big users of QSC and, surprisingly, Behringer (neither of which I represented). Personally, I would suggest renting a few different models and brands, and trying them out before you buy. Many PA shops rent what they sell, or can point you to someone that does. Plan to spend around $499 per speaker when you buy.
4. Stay Away from the crap that American Audio (American DJ), Gemini, Samson, Peavey make. It's all garbage, move along.
5. While it does't hurt to give Ben NLFX (I don't know him, but everyone else here seems to speak well of him), give your local shop(s) a chance at gaining your business as well. Remember, you are asking your community to support you, and you should make an effort to do the same, within reason of course.
6. Pick up something used. One of the best places is Rental/Production shops that are turning over inventory. Those type of companies typically keep their gear well maintained, and usually there is still warranty on the product. When I was in the production business, I turned over our rental inventory no more than every 6 months, allowing me to keep new product in rentals while getting a decent dollar for the used gear as it was still in excellent condition and had lots of warranty time left. You can also keep an eye on places like Craigslist, Pawn Shops, eBay, etc. for used gear, but you need to be careful and ensure that the product is in good condition and full working order.
Good Luck!
Clinton