We are an IT company with lots of experience, though only recently a member of Freelancer.com. We provide professional software design and development services. We have several years of experience designing, developing and administering web, desktop and mobile applications on all major platforms in a variety of languages.
We have read your list of requirements and it is a straightforward project. We plan to create a simple to use web page with all the required forms, with a PHP script that will receive all data and proceed to create a copy of the PDF files with all data filled in. Alternatively those could be sent to a predefined email address, if their size is not too large. This way the main form can easily be edited, as HTML/CSS/JS are very flexible in this regard, allowing for complex rules on which fields are enabled/disabled and what options are available.
A Windows or Linux server will be required, but there will be little performance requirements so a cheap VPS from a reputable hosting provider would be enough.
We can discuss the project futher via chat. We are looking forward to collaborating with you.