Dave wants to know if Leo likes the Amazon Kindle HDX tablet. Leo does, and it pays to look at reviews before buying them. On Amazon, he can get good reviews from people who actually use the item. Toss out the high and low reviews, and he'll have an accurate depiction of how the item works.
If Dave likes the Amazon ecosystem, the Fire is a great option. But if not, then Leo points to the Google Nexus 7. What about adding a keyboard? Leo says that any tablet will work with any bluetooth keyboard. So he can just get the one he likes.
Dave wants to be able to put cassette tapes onto his iPod, and for that Leo says he'll need a computer. There are also dedicated devices that will digitize old media. Dave can find some of this at crosleyradio.com.