Is it weird that we're discussing a "seperation" date?

Not weird... my wife and I agreed on a January checkpoint also.

We agreed once again this month to a "new" marriage path so this is a check-up of what happened since Octobers Talk.

We may still end up divorced but will set up additional checkpoints as needed until we resolve on way or another... they will get more frequent as we move towards my self-imposed year 4 deadline since ILYNILWY. January... March...April...May... you get the idea.

Pretty sure things will resolve from sexless to sexual so we can stop the checkpoints.

Perhaps do like I'm doing and do a distant.... final decision point. Mines 13 months away. Gives us both a chance to work on things from respective ends

This is much of what therapy would advise. Helps if you can gain commitment though.
If there is any Love this may be the way to go...if not you should just get it over with.

Agree learn how to argue constructively from here until January.

Heck I gave my wife an agenda via e-mail before our October talk so she knew what the topics were. It helped as I gave her time to think about what she wanted to say. She realized she couldn't squirm out of it is time we talked for well over an hour. Gained solid commitments and agreed on the future checkpoint.

Marital impasse resolution 101

One thing I notice... in having discussions over the years... you do get a sense she is listening more. Sure both spouses are interested in resolving an impasse...makes sense. pretty sure January's conversation will go smoother as we can reference the work done in Octobers one. I hope for some sex results in-between... doubt she'll want to go into that conversation still sexless.

Take charge and affect change.. control YOU.