WTB popcorn and a lawn chair to sit back and watch the trolling begin!
Seriously, are you asking a question about the game or just complaining about it? It is possible to reach the max level with bad gear; it's whether you want to do some of the harder content that matters. Leveling a toon is difficult from the 55 to 64 range; before that you can go through most of the content with quest gear. Starting at 55 is when you want to start spending time and money on getting good gear and weapons. After 64 you can roll through quests but it does get harder if you're still using bad gear.