Roger wants to be able to record music and play with images. Would the Chromebook be a good option? Leo says that he can do it on a Chromebook, but it's all mostly done in the Cloud. The problem is that it needs an always on internet connection, and it's not really that easy for higher end applications like music recording. There are some Chromebook extensions that can do it, however. A good way to test it is to use the extensions on his existing computer. SoundTrap is one. If Roger can do it on his existing computer, he'll be able to do it on a Chromebook.
Another option is Roger's iPad, which can record via GarageBand for free. He'll just need some hardware that can allow him to connect it. Leo recommends the Shure MV88, which will plug right into the iPad. If he wants to record a guitar, then iRecord is a useful interface to record instruments.
Roger's SmartTV has a frustrating interface. How can he connect his iPad to make that easier? Leo says he can't do that unless he uses an Apple TV. But there are some TVs that do support Bluetooth keyboards.