Ask the software vendors for specification sheets that list what their programs will do. That alone will get you thinking. The price of a program should not be a restriction as much as a guideline for what it is that you're looking to get out of your investment. As a rule, the more functions and utilities your situation requires, the more you should plan on spending. Look closely at the fine print.
Technical support can be very expensive.
Computer programs are becoming so easy to use that someone who has never seen a computer in his or her lives can be shown how to navigate the Internet or send e-mail in minutes. If a program is not suited to your level of computer knowledge and ambition, then chances are that eventually you will not want to use it or at least not to its full potential. Ask the vendor for a demonstration sample and find out if it's something that you're comfortable using. If you have to go through several steps and sub-programs to find what you need, then the program is not responsive to your needs. That is the test for user-friendliness.