Playing my music in the most effective way - after some help!

Hello
I'm new to this game (technology!) and have a couple of questions that I would appreciate any help with to make the most of my iPad Christmas pressie!
Firstly. Can I upload my external hard drive of music onto cloud and is there a maximum. I have about 300gb of tunes on the hard drive! I would obviously like to then play through iPad.
Secondly, I would love to play the above tunes on my stereo system. It's quite old school but a great set of speaker and amp, Now the mrs has put the stereo away in a cabinet so not easy to get at! One option I was thinking is to get a Bose speaker that can work blue tooth. Does anyone know if I can connect the Bose to my old amp so also run off my wall mounted speakers at the same time. Not sure if it works that way round. Or any other advice
Any help massively appreciated
Cheers
Luke

I just realized I have a different iCloud account set up on my phone. The one on my Macbook is the one associated with my ITunes account. Could this be the problem?

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