Best way to implement Enums with Core Data

You'll have to create custom accessors if you want to restrict the values to an enum. So, first you'd declare an enum, like so:

typedef enum {
    kPaymentFrequencyOneOff = 0,
    kPaymentFrequencyYearly = 1,
    kPaymentFrequencyMonthly = 2,
    kPaymentFrequencyWeekly = 3
} PaymentFrequency;

Then, declare getters and setters for your property. It's a bad idea to override the existing ones, since the standard accessors expect an NSNumber object rather than a scalar type, and you'll run into trouble if anything in the bindings or KVO systems try and access your value.

- (PaymentFrequency)itemTypeRaw {
    return (PaymentFrequency)[[self itemType] intValue];
}

- (void)setItemTypeRaw:(PaymentFrequency)type {
    [self setItemType:[NSNumber numberWithInt:type]];
}

Finally, you should implement + keyPathsForValuesAffecting<Key> so you get KVO notifications for itemTypeRaw when itemType changes.

+ (NSSet *)keyPathsForValuesAffectingItemTypeRaw {
    return [NSSet setWithObject:@"itemType"];
}

You can do this way, way simpler:

typedef enum Types_e : int16_t {
    TypeA = 0,
    TypeB = 1,
} Types_t;

@property (nonatomic) Types_t itemType;

And in your model, set itemType to be a 16 bit number. All done. No additional code needed. Just put in your usual

@dynamic itemType;

If you're using Xcode to create your NSManagedObject subclass, make sure that the "use scalar properties for primitive data types" setting is checked.