I am a Computer Graphic Arts / Systems graduate with a small event photography business. Business has grown recently to the point where I am starting to need a way to track clients and handle information and mailing. I do a lot of memorabilia-related jobs where I will go and shoot the group event and take orders for DVDs from the attendees. It works great and the sales come in, but it means that instead of a 1:1 client/job ratio I get about a 80:1 ratio on average. I can end up with 100's of new clients a week and I need to keep their information around and generate labels so I can ship them their orders. I also do traditional and commercial photography and need a system that can handle those needs as well. With my systems background I know I could code this thing in a week or two and customize it to my needs and wants. I would much rather look for a commercial system that can suit my needs than go that route, however. So, I turn to you guys to see if you have any suggestions. Below is a list of needs and wants and I'll do my decision analysis based on this requirements list. Needs: - Must store client data (name, address, phone, etc...) - Must be able to create jobs and assign multiple clients to said job. - Must be able to attach clients to multiple jobs. - Jobs and clients must be able to be tagged with notes. - Must have a fast interface. Either cocoa app or web app with lightweight interface. - Must have an advanced search feature to find clients or jobs on any term. Wants (rated 1-10, 10 = most important): - Skype link to phone # embedded = 3 - Generate pdf labels for a single or arbitrary group of clients = 10 - Calendar integration with iCal or google calendar = 5 I made the list as simple and loose as I can. If anyone can think of anything that would fit my needs or something tailored specifically to photo client management, let me know.