Property Management System that does what you expect is hard to find. Using a software package that allows you to take a tenant from the beginning (first contact with applicant) to end (tenant moves out) will allow you to stay very organized and have one central location for all your information on your tenant.
When you are evaluating a property management system, be sure that you have a "wish list" of what you expect the program to do. Be sure not to be distracted by a property management system that has many "bells and whistles" but doesn't have the core functions that you require.
A good system should work with you, and not just introduce more hassle into the process when you're already overburdened trying to keep your business afloat. A good system should be seamless, eliminating a lot of the paperwork drudgery that a manual system keeps you tied to.
One way to start is to make a checklist of everything you already do when managing your properties. That will help you keep in mind all the issues that you want to solve, to improve your efficiency. Only then can you make a proper decision. Many salespeople will try and sell you whatever solution makes THEM the most money, but it may not be right for you. Don't be afraid to go down your list point-by-point and make sure their system does what you need. And also look at what feature they're trying to push on you that you don't need. There's no sense spending more money on something that is overkill for your needs.