Difficult, but not impossible

You chose the Cobalt Tower for a few reasons. It was one of the only dragon hoards you could reach in any reasonable amount of time without a horse, and the tower wasn't originally built to house a dragon. The Cobalt Tower used to be the home of some mad inventor some generations ago, from your campsite across the field you can spot the copper cage on the roof that was rumored to catch lightning. The point was that the tower was made for a fragile old man to get around, not designed from the ground up to be a test of worth for knights. From the rumor mill and any books on the subject you could get your hands on, there were no traps in the tower. Just the dragon and the princess.

The dragons name was Freyr. There were many accounts of him. He had guarded a different tower for some other kingdoms heirs for a long time. Fearsome and powerful enough to outlast generations of knights, eventually the princesses began to grow old and infertile which went against the point of the whole system. A deal was struck with the dragon, he would get to eat the barren princess on the grounds that he leave for a less deadly dragon to take his place.

That was two hundred years ago. The Cobalt Tower is less of a place to guard and more of a place of retirement for him. You're hoping this means he won't be expecting any visitors.

Elysion Gersemi, the princess. Or queen, depending on which side of the bar fight you were on. For most of her life there was nothing truely of note, she was oldest daughter of a king and thus put in a tower as was traditional. Then she was rescued by a brave knight (Sir Peter, if you recall) and promptly refused to marry him for reasons unknown. She fled her own wedding, and sequestered herself willingly in the Cobalt Tower as to discourage her fiancé following. The fact that she was rescued, and thus obviously to be wed to the knight that did it, and simultaneously unwed to him as she fled the altar, was a large source of political strife to the kingdom she hailed from, and had been for the past nineteen years.

With a princess (or queen) who was no longer young and didn't want to be rescued, as well as a dragon too deadly for the system to handle, its no wonder no one wants to storm the Cobalt Tower. Except you. You're hopeful that you can get away with just some gold. The princess has to eat, and during the two weeks you've been staking out the tower you've seen the dragon take to the skies to hunt for her. Should the rumors hold true, the treasure should be completely unguarded then.

You take another bite of the rabbit you were cooking on a spit, watching clouds go over the tower. The sad truth was that hunting for yourself in the woods for the past month has provided more food for you than working on the farm. It was a bit of a problem. The hunting leathers were your fathers, and he had been a tall and thin man. You were tall yes, but after a month of eating well your feminine features had filled out again, making the outfit a bit tight around your chest and rear. You clean up you lunch wondering if you should change back into your overalls. The leathers were the closest thing you had to armor, but the more comfortable clothes might be easier to move around in.