Automatically sync local files and iTunes playlists

[herrsmith]

I want to be able to listen to my songs that I maintain in iTunes on my Android phone.  Google music seemed like the ideal way to do this, but despite having an official app that automatically keeps the two in sync, the playlist limit of 1,000 songs is just about a dealbreaker.  Now, I'm hoping to use Spotify instead.

Is there any way to essentially slave Spotify to iTunes so that I can stream my music from anywhere, and download the occasional playlist to listen when I can't stream?  It doesn't need to be perfect.  I'm willing to accept a few songs that don't quite match, and a few songs that don't quite match up right.  Is there even any way to put my already-made playlists into Spotify and update them whenever I feel like changes have been made?  I've tried all of the services listed online (https://support.spotify.com/us/problems/#!/article/Convert-Playlists-to-Spotify), but Playlistify.org doesn't load, Ivy claims my library (10 MB .xml file) is too large, Unify says doesn't work with the updated version (it's not even clear when that was posted), and Soundiiz says it only works with other streaming sites.  Is there no official program to do this?  I'm surprised how difficult it is to even start using Spotify.

If what I want isn't possible, does anybody know any useful music streaming services?