Hello,
It is nice to see a detailed specification.
I can develop the solution in ASP and Access, however, have you considered alternative technologies?
My recommendation would be a JSP/MySql combination (using open source Tomcat). This allows for greater connections to the database than Access, and depending on future usage and availability requirements the system can be redeployed using products like BEA WebLogic and Oracle.
For the reports that you want drivers to sign I would recommend getting the site to generate them in PDF as this will produce better printed output than HTML.
Regards,
Gavin Grayston