Joel Spolsky on when to build and when to buy software.
If it’s a core business function — do it yourself, no matter what.
Pick your core business competencies and goals, and do those in house. If you’re a software company, writing excellent code is how you’re going to succeed. Go ahead and outsource the company cafeteria and the CD-ROM duplication. If you’re a pharmaceutical company, write software for drug research, but don’t write your own accounting package. If you’re a web accounting service, write your own accounting package, but don’t try to create your own magazine ads. If you have customers, never outsource customer service.