No contest AT ALL. A Rega setup will crush anything out of iTunes any day, regardless of genre, period!

Obviously all the usual divides will apply for conveinience, portability and the like. But for great sound and the joy of having that nice 12" cover in your hands, it's no contest. Plus, if you are anywhere near some decent used record stores, there are mountains of treasures to be had for absurdly low prices.

But u still need speakers and amp to play the vinyl, so sure, go for the PSB's and Marantz. And of course u still want to play the music u have and will continue to get in iTunes, so plug that in too. Delay the HRT Streamer if you need to, can add that later while u still play iTunes into the amp (and/or into headphones) from the Mac headphone jack.