I just want to shake him! I feel like he's making positive moves with you, and yet he's too afraid to act on it and stop this silly D talk.
Well, what are your thoughts about the stlmt form and financial disclosure? Is there a timeline? What's the consequence if you don't? Maybe it's time to see an atty for some input here... Seems like you can find ways to comply as you have to, not cooperate too readily.
I think he needs to miss you... he can see how great you look, how confident and that you're a great catch. Maybe it's time to really drop the rope and GAL and let him miss you and the good interactions you've had lately.
As far as the ring, I'd suggest giving his ring back to him. Who knows why he wants it, but having it with him vs. you may serve to as a good reminder of your bond. If it comes up about you taking yours off, maybe something to the effect of 'our old M is done'. If we decide to work on us and start a new M, I'd love to wear my ring again'.