I take the simple approach to holidays, do not get tangled in the materialistic BS. My nieces and nephews get spoiled, Christmas is for kids. I just like going for a ride and looking at the lights or going to dinner with friends. Spending time is much more important - everyone's life is so busy.....
Tim, your patience is beautiful. I really wish she'd just go to MC so you don't have to do this all yourself. Trying to determine the right time to bring things up knowing that if it's not the right time, you've taken 5 steps back...... Not fair. IMHO you have been doing a majority of the work for quite a while. She has some pretty firm boundaries in place and she's not budging unless she feels she may have pi$$ed you off. From a friend standpoint, you both are doing great.
I'm concerned there's never going to be a right time. A few week's ago there was flirting which you handled very well. Do you feel there's been more of that? Maybe I'm being too hard your W based on knowing only what you put here. If that's the case, forgive me.
I hope you keep posting and that you stay safe in this goofy storm we're supposed to get tonight. I hate ice!