Small world!

If you want to set up a recurring action in OmniFocus, you'll find it in the Inspector panel towards the bottom. Works a treat. If you're using the Mac Calendar, I'm not sure you can have repeating to do's - you could probably use a repeating all day event or use BusyCal which does have repeating to dos. Since you want to keep it all in one app though, I'd try OF first and see how you get on with it.

I only started using Way of Life once the habit is ingrained enough not to need a reminder at the time - I just check off about 20 habits at bedtime to keep that general awareness.