Congratulations on your perseverance...though I really meant what might not work was the D/s thing, not necessarily the relationship. It's certainly easy to over think things. These activities are supposed to enhance, not distract, from a relationship. Confining chastisements to areas generally covered by clothing is easier during the winter - more area to work with. Keep it light and fun...at least to start.
New Concept - RENT-THE-OZ!