I've just bought the game recently and found Judy to be a very reasonable and helpful quest giver and team leader, she is clearly experienced but turns out on the helpful side on various occasions, even though this opened up new avenues of risk.
At the end of the Clouds fiasco she noticeably just 'gives up' and that's where our romance happens, even asking if she would have the night together with V and forget about the firefight that just went on.
I think at this point the narrative or continuing relationship should be a role-reversal with V taking Judy out for quests, visiting Clouds & Afterlife or doing merc and netrunner jobs for the establishments together. Giving V a leading role in the relationship and telling Judy "never give up" - not using her escapism just to get in her pants, so to say. We should have some responsibility and reward to check on her apartment from time to time, where J would do her usual thing of leaving breakfast surprises or other gifts.
I liked how Panem would actually reject advances which I think she would do in similar situation, demand the player's help in getting revenge, and not skip town just because of a string of misfortune.
Maybe there should be a future story (or a player-crafted mod) enabling us to put two of them together while V takes a step back and does what they're supposed to do in the main story