Not be able to access type override object properties?

You can further extend the extended_seq_item class adding or overriding more constraints. Then you can replace the factory override with that extended class. (or some other mechanism that overrides the override).

You can also extend your test_sequence class replacing the body method to have a new randomize with constraint.

I prefer the first suggestion and not use the with clause. It is in better keeping with object-oriented programming practices.