User groups and telecommunications services are loaded with experts advisors on a variety of computing issues. Whether or not to upgrade is probably one of the hottest topics on the roster of debates. You'll have no trouble finding someone (or hundreds of someones) to give you advice. The trick is to evaluate that advice with your own in mind.
On telecommunications services, look for people who not only know what they're talking about, but who also know how to speak at your level. If you know exactly what you want and you're an experienced user, you need to talk to someone who can appreciate your needs as a power user. Beginners need advisors who can speak their language. If you wander around the telecommunications services extensively, you'll find discussions that resemble religious wars over which microchip is in and which will be extinct in a few days. Use these battles as background; most are based on opinion as much as on fact.
In user groups, watch for the people who enjoy taking less experienced members under their wings. Also, keep an eye out for special seminars on upgrading.
Besides people contact, try software contact. COMPUTE!s PC Magazine will publish an article on upgrading your computer in March that will be accompanied by a program that tells you how much your dream computer will cost. In the process, you'll learn a lot about your options.