Selfhosted

What I'd do is set up a simple website that uses a little JavaScript to rewrite the date and time into the page and periodically refresh an image under/next to it. Size the image to fit the remaining free space of however you set up the iPad, and then you can stick anything you want there (pictures/reminder text/whatever) with your favorite image editor. Upload a new image to the server when you want to change the note. The idea with an image is that it's just really easy to do and keeps the amount of effort to redo layout to a minimum -- just drag stuff around in your image editor and you'll know it'll all fit as expected as long as you don't change the resolution (instead of needing to muck around with CSS and maybe breaking something if you can't see the device to check that it displays correctly).

There's a couple issues to watch out for -- e.g. what happens if the internet connection/server goes down, screen burn-in, keeping the browser from being closed/switched to another page, keeping it powered, etc. that might or might not matter depending on your particular circumstances. If you need to fix all that for your circumstances, it might be more trouble than just buying something purpose built... but getting a first pass DIY version working is trivial if you're comfortable hosting a website.

Edit: If some sample code that you can use as a starting point would be helpful, let me know.