Hi Nathan,
Using Dynamic Login, you can go to the Control Panel and in Module Configuration, you'll find "Force Profile Change." Just make sure that the profile property is set to required from Admin, User Accounts, Manage Profile Properties.
However, this will only work if that property remains blank. If you want them to answer questions every time they log in, you might want to use the Default Redirect Link in Module Config or use Security Role Rules for the redirection. This will bring them to a Dynamic Forms page with the questions that will then redirect them to the Tailored Text/Html.
Hope that helps!
Candace