Segmentation rules ONLY work against xDB contacts. If you have any properties in the user profile (aka asp.net members profile properties), then this will never work. You need to push those properties to a custom xDB facet.
Segmentation rules are just predicates that are added the xDB search query.
You need to register your custom field in ~/App_Config/FieldTypes.config. Once done, rebuild the Link Database.
From this point on, the field references will get updated automatically when the item updates.
We had a very similar scenario with a custom image field inheriting from Sitecore Image field. Tried all of the above, without any success whatsoever getting the references added to link database.
The way we solved it was to use the namespace for the field we inherit from when registering the field type within <fieldTypes>:
<fieldType name="Our ...
The Experience Profile and List Manager interfaces rely on personal data being available in the xDB index. As the FirstName facet is marked as [PIISensitive], you will not be able to use it by default.
To use contact facets marked [PIISensitive] in the custom predicate, please enable indexing of PII sensitive data in the xDB index.
I am able to see the ...
It turns out that for the Form editor to work, all field type templates must have a standard values. By decompiling the DLL that contains the action for the API controller for the SPEAK interface of the form editor, I found that internally it runs a pipeline, and the first processor has an Assert that throws if the template for the field type does not have ...