Hi cadbaros,
The best way to create an attractive and useful solution, within your limited budget, is to use a FileMaker Pro database.
FileMaker gives us the checklists you want, with the option of having built-in lists, and lists which the user can create themselves. A "signature" field can be added, and the completed lists can then be printed or emailed (for example, as a pdf).
I would create the database on a Mac, and the file is then emailed to the user's iPad, and opened in the (free) FileMaker Go app.
I would be happy to discuss this further with you, and if you are interested in this solution, we could design a small demo version for you to try out before you decide to award the project.
Best Regards,
- Rob Dixon.