Hi b-jazz. 
I will try to advocate for the tool to be updated. Unfortunately, I seem to be one of the only people in my community interested in fixing this problem, and our community is just as massive as yours. And the tool was made by one person who I am not close to since I am fairly new to this community. Again I will try my hardest for this change to be made, since like you, I want OSM to look the best it can be. 

If I may be so bold, no one has ever told me why lollipopping is bad. I understand very well that it is bad, but every person I've heard, whether from my community or yours has only said that it's bad. Why is it so bad? What exactly does it break in OSM for it to be considered bad?

I do want to continue to be a helpful part of the OSM community and all I ask is for a small amount of leniency that I am trying to be as rule-abiding as I possibly can. Even before this interaction I have been trying to make as few lollipops as possible while still being able to get the data I need and trying to fix them afterwards. I also would like to mention that I have fixed the area in question of anything that even remotely resembles a lollipop. I understand that this is probably not enough for you but all I can promise to do is to create as few lollipops as I can and as you say, take the "Eventually fixing them," out of the picture. And fix them as soon as I have exported the data I need. 

I understand this is probably not enough for you, and again all I ask is for a small amount of leniency until such a time as the tool has been changed. I would like to finally add that I am not one of the people you should be after since I am someone who genuinely cares about the state of this issue and I'm not one of those people who leaves awful lollipopping edits lying around. I have even encountered some of these myself and I have worked hard at fixing them for the good of the OSM community. 

Finally, I went back through the terms of service and I realized there's  no ruleset there about things like lollipopping. I'm wondering whether it would be wise for some of the moderators to come together and create a ruleset to add to the terms of service to help with this problem. obviously, it won't fix all of it, but it will help.

Thank you for your time and effort in moderating OSM and I hope that this resolves my particular situation.