I don't think the server needs big changes. Just some simple stuff, like a welcome message that tells you in a few short lines where to buy (spawn)weapons and how to make cash. It's important that people read this when they ENTER the server, so they really can't miss it. This avoids people are going to ask questions how all the important stuff works, or that they will leave the server because they don't get the point. So for example, if someone who isn't registered enters, he/she first must read the few simple lines (and rules) before he/she can play. Not only in big text the server rules, but also how to buy weapons/earn money. Most people are too lazy to look at /help, maybe some of them will watch it, but most users ignore it if you ask me. In another topic I saw a suggestion of increasing the money on registration, also this is a good idea. I think 50 or 100k should be enough to start buying some properties.
The simplicity of LW's made me come back to the server, so it should stay simple. No complex system of advantages, skills or differences in pricing of products. Only you have to make sure that lazy people come back. Give them a bone to play with...