Scott has an iMac and MacBook Air and he is concerned about upgrading to El Capitan because it may break some of the software he uses. Leo says he should always upgrade to the latest. The upgrade is really easy to do and it doesn't break many utilities. He could roll back if there is an issue, but Leo says he probably won't have to. Some really old software may have issues, but that's only if the software is reliant on the old Rosetta interface, which Apple killed a long time ago. So anything written in the last few years won't be an issue.
Scott is thinking about getting a set of Bose speakers. Leo says that he'll either like Bose or not. And if he likes it, then it's a good, albeit expensive choice. Another option is JBL's Extended range speakers or B&W's Zeppelin series. Getting it with Bluetooth is the best option, but a dock will do as well.