iTunes to Spotify Migration Questions

[jenks42]

Hi, I'm on the fence between switching over everything from iTunes to Spotify Premium. I do NOT currently have Premium. I have spent some time looking around this website looking at iTunes to Spotify posts, but still have specific questions. If I make any incorrect assumptions leading up to my questions, please let me know. Thank you in advance.

• It appears there are two ways to access any iTunes data through Spotify:
  1. Spotify --> Preferences/Settings --> Local Files --> iTunes
  2. File --> Import Playlists --> iTunes

From my understanding, it appears that option 1 uses Spotify as a music player to play the files that are on the hard drive. When I add a voice memo from the section Local Files to a playlist in Spotify, the "Local Files" symbol appears next to the song. However, when I add a "normal" song from an album that was ripped from a CD or bought on iTunes to a playlist, that symbol does not appear. I also have the ability to "Save to Your Library," with those songs, which did not appear when I right-clicked on the voice memo. Is that because Spotify was able to match that song to their online catalog? When I play a "normal" song, is it playing from my hard drive or the internet? (I assume it is the internet because the only songs accessible when I turn the internet off on my computer are the voice memos.)

Option 2, on the other hand, only imports playlists, along with the songs in them. I tested to see if it would import a song in a playlist that was a voice memo, and it worked, with the same "Local Files" symbol aforementioned. However, it does not show up online. 

In any case, when I try to use the online player to play any of these iTunes songs, I can't play them unless the Mac app is open. Why is this? On my iPhone, I can play them, but only by shuffling them. Why is this? (I assume this is because I am not a Premium member yet.) If I switched to premium, would either of these things happen?