ITunes Library too large - options

Hi there
I'm looking for some suggestions to help me free up some much needed space on my MacBook. I have a MacBook Pro Retina with 512GB with a 64GB Nifty Minidrive but I'm running out of space. My iTunes library is taking up over 330GB in music alone (it's mainly music and some apps as I don't have too many videos).
I've done some reading on the web and as far as I can tell I have 3 main options:
Move the entire library to an external drive
I've done this before (many years ago) and I recall having permanent issues with files if I accidentally tried to access the file if drive not available. Also, I'd like to have at least some of my content with me (i.e. I don't want to have to carry an external drive with me all the time or have to have web access to listen or transfer media)
Move part of the library to an external drive
I think this is my preferred option. I've read several articles about people moving their video content on to an external drive. Unfortunately for me I don't have much video content so I would be looking to move some of my audio content away. I was thinking of moving the compilations (currently 130GB) but I don't know how this will work should I choose to add a compilation album later? I presume I would have to add to iTunes and then manually move it across to the external drive. I'm thinking things could get messy!
Create a second library, located on an external drive
This is a bit like option 2 but from what I can tell it means you can no longer have music from both libraries on the same iDevice. Is that correct? It also has the pitfalls of having to maintain the two locations so I've discounted this unless anyone can see why this is a good option.
I'd like to hear your comments to the above or any additional suggestions you might have. I don't want to buy a new Mac just yet (will definitely get a much larger drive next time). Just so you know, I have Amazon Cloudplayer but as I'm in the UK I can't access this from the Mac app (can access via web and iDevices though). I have around 50,000 tracks so iTunes Match and Google Play aren't viable options for me. I have Dropbox but I only use this for documents and photo backup. I also have 2 x WD My Cloud network drives at home for backup, remote access and for my Sonos system. Thanks.

Spotty comments/observations:
If adding an item to iTunes, hold down the option key while dragging the item to iTunes. It will leave the item in its original location.
I have multiple libraries (mostly for testing). However, I manage my own media. One potential issue with multiple libraries is if you use iTunes "copy media to media folder" checked (default setting) and you have one library on the external and the other on the internal drive, iTunes still only uses the same set of preferences settings. In other words, your media for one library end up going to the wrong place. Of course you can do as I do which is manage my own media, but that's something to consider. To be honest, I don't know what happens if you leave "copy to" unchecked but "organize" checked. I have always from day one had both unchecked. It puts the onus of managing media on me but it also means I can have media wherever I like.
Yes, iTunes has conniptions when an item on an external is disconnected. However, it is usually relatively easy to remedy the situation by quitting iTunes, turning the device on, then starting iTunes again. If your whole library is on an external drive and iTunes defaults back to the internal drive, start iTunes with the option key held down and point it to the external.
Look into iTunes Match for travel use. However, with 300 GB of music that may mean you have more than 25,000 tracks. I guess Apple figures not many people can afford $100,000 of music (or even $10,000 if it's in lossless files) and don't accommodate for that in Match.

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