I've been using Chrome OS for a while now and while I wasn't on the first-generation of Chromebooks, I have been using them since the second generation. One thing that makes them great is their simplicity, but this is also a bit of a flaw. Things like managing your files on the Chromebook has been tedious - and next to impossible, but that is changing with the latest update coming very soon. You will finally be able to manage your stored files - much like you can on a Windows PC. This is a nice and much needed addition.
You can get your total free space via the Files App, but that doesn't give you any info about how it's being used. It can also break things down file-by-file, but that can be too much info for many folks. Luckily, Google is about to unveil a storage manager for Chromebooks that gives you just the right amount of info at a glance, according to insider François Beaufort.