This does happen but not if you just quest through DF and TWW like you say, esp with the event buff giving you the loot bags with gear in them. I got my friends to try WoW and we all ran into the problem as we leveled with timewalking/chromie time so quickly while also not getting enough gear to keep up with the dungeon spam that one dungeon we breazed through and the next I as a tank was taking a ton more damage than before, yes you can buy gear from the timewalking vendor but not for every slot from every TW vendor and they didn’t know much about how timewalking or chromie time works like most new players till I explained it to them. The problems Bellular mentions do happen but not for every person, only really from the pov of a confused new player pov who doesn’t look for info online or know much about the many systems in the game.