1) It is recommended that you should use MS SQL or MySQL for this kind of application so that you can store images
2) You should use tomcat version 6
3) JSP/HTML provides nice and easy to build GUI.
4) If you want to use java files with main method then you will have to develop the desktop application.
5) Using servlet is good approach while developing applications, you can use them to process the business logic, and you can use JSP for GUI.
6) Servlets are multithread, i.e. you can use them to build multi threaded applications which will handle multiple clines at the same time.