Here is something that you don't know unless you have the walkthrough, or go through 40+ pages of this forum, that you can't go to anywhere but your apartment, apartment building, and the university. You can't go to meet your sisters, your mom, and a few other places until you unlock it via doing the Dana story. Using a walkthrough also avoids wasting resets. And knowing where to start a time line, change them, etc. Going through blindly means that you don't know these things, until you either search through everything on here, or find a walkthrough. And it does need updating.
There is no such things as wasting resets... not when there is several achievements tied to number of resets (highest requiring 1.000 resets).
As for Dana blocking access to other stuff... it's been awhile since I played since begining, but you could always go only to Apartment building (where your apartment is) and University at start. And you only had Alice and Dana "unlocked" by the end of that first run which end up with you being hit by the car.
That first run gives you a few starting points (Dana, missing teacher, gym fight, drugs, lab vandalism) with Dana being the most "logical" start. But you used to be able to follow other options... that said, you weren't able to go far with them without dealing with other stuff first due to lack of skills (or in some cased because it was still "under development"). If that is no longer possible then it's recent change. Mia (and the Mall) was "unlocked" once you reached Day 1 evening when you got her text message about not meeting her. Lisa and Mom could only be unlocked after talking to Mia (and Mom can't be unlocked on Day 1 no matter what).
Yes, WT is good for giving you a useful points to create a timeline, but everything else you'll be able to figure out relativelly easy IF you bother to read text so you'll know what is going on.
As for WT update... Kamelkido used to publish his version of WT for public version (currently 61.xx), but he stopped making one when author took over few updates ago. So unless some patreon paying $15/month to get current version of the game and WT (64.xx) decide to post both, I wouldn't expect any updates for either game or WT... at least until version 63.x became public sometime in July/August when we'll get new verion of the game (but not new verision of WT).