I used to try to play like this, but I have gradually tried to move away from it since I feel like it is easy to just treat the whole game as one big task that needs to be finished. Like every quest is another task you want to just be over and done with and also it can get a bit stressful to always try to do everything right, pick up everything and talk to everyone and on top of that do all the "right" decision without even knowing you are. It can quickly lead to me getting a bit anxious.. It is hard though to step away from it since it is so ingrained.
I have instead tried to go toward a more roleplaying approach and since I love consequence I will probably start playing Fallout 4 as Dead is Dead so that pretty much works against a "perfect" playthrough. I actually hope you can't actually do everything with one character, like you could not please everybody in Fallout New Vegas. Its possible I would do something like that at some point, but when thinking about it though I don't know if I really want to 100% the game since that takes away the "magic" a bit of discovery when you know you have done "everything". It is nice to know you never know if there is something new out there you have not seen. How do you plan to go about knowing when you have 100% btw? There is no % stats in the games, you know of some good guides for it?
I will probably take manual notes of some things though over many playthroughs, like bubblehead locations. Since I will play DiD and my characters most likely will die before they can gather a full collection it could be fun to keep track of the ones i find to gather them all with some character later. Also if you wanted you could always load up an old character and take notes of what quests he have completed, then make a big list of all quests in an excel file or something for all characters. That way you could play quite freely but still have a "100%" quest finish (an a real 100% since you could do it for all factions) over many characters instead of one. You could have a crazy collector character that tried to gather all bubbleheads and other things, maybe building a museum in the wasteland, then another character that does the main quest, then another that is an explorer etc. After their adventure is done you could record all their quests and findings in a big document and get "100%" perfect playthrough that way. Just an idea. I will probably keep track and keep some "mementos" of my characters that way.