First of all, you have one lucky BF to have a friend like you!!! You have many options for a room under $300/ night and many that would have that magical feel you are looking for.
The value resorts (POP and the All Stars) are all very Disney-themed resorts. They all have huge icons scattered around the property, like 4 story tall dalmations at AS Movies, 4 story tall cowboy boots and drum sets at AS Music, an unreal huge big wheel at POP, and many others. Everything there is bigger than life and very brightly colored. They are just too fun!!! We stay at lots of the Disney resorts and go back to the values for the fun of it all and not all for the money. From the values, you would take the bus to each park. If you want her to have that 5 year old feel, then a value resort is definitely for you.
The moderates are great also, but are bigger and have slides at their pools. Of all the mods, we prefer the mansions section of POR. We love to stay there too since it is really relaxing!! It looks like it is right out of Gone with the Wind. From the moderates, you could take a boat to DTD or a bus to the parks.
The deluxes are great resorts and are closer to the parks with various travel options. They are a little more plush, have queen size beds instead of full like at the other resorts, and tend to have more table service dining options available. The cheapest of the deluxes would be AKL and WL and with January discounts, you could possibly get a room for less than $300/ night. Of all the deluxes, we prefer the BC for it's closeness to Epcot, BW activities, SAB, and Cape May Cafe character breakfast.
Have a great trip!!!
