What are the pros and cons of owning a Chromebook? Considering purchasing one but have some questions

@julde  I forgot to add earlier that if you want to test the Chromebook experience without having to buy one first, there's a potentially easy way for you to do that using a product called Neverware CloudReady, link here.  Neverware offers a slightly customized version of Chrome OS, which is free for personal use, and their CloudReady product basically allows lots of popular laptop models to be turned into Chromebooks, even just temporarily and reversibly (keep reading).  Some people do this with old laptops that might not be great performers in Windows anymore but would perform perfectly fine as Chromebooks.  That scenario involves installing CloudReady onto the laptop's internal drive and replacing whatever was there, but potentially better for your purposes at the moment, if you have an 8+ GB flash drive, you can install CloudReady onto a flash drive and then just boot the laptop from that flash drive to use Chrome OS on your laptop WITHOUT having to replace whatever is actually installed on the laptop's hard drive.  You'll still need to make sure that you have a laptop model that's "certified" because otherwise CloudReady might not be able to work with that laptop's WiFi adapter and such, but Neverware maintains a list of known working laptops.  So if you have one of those at the moment, create a CloudReady flash drive and boot your laptop from that, and you'll be able to see what the experience would be like.  And if you don't like it, just disconnect the flash drive and boot that laptop normally, and you'll be back to whatever that laptop had before.

If CloudReady is a bit more than you want to get into, then if you use Google Chrome, think of Chrome OS as basically just that, because that's essentially all it is.  If you can do it in Chrome, then you can do it on Chrome OS.  If you can't, then odds are you can't do it in Chrome OS either.  But remember that Chrome OS also gives you access to Chrome plugins, which can add a lot of functionality that you might not be using in your Chrome environment today.  For example, the Offline mode for Gmail and Google Docs is a capability that exists even in Chrome running on Windows, though not everyone chooses to use it.  So just because you might not actually BE doing something today in Chrome doesn't necessarily mean you CAN'T.

@julde I can't speak to being able to access your iTunes library from Google Music, but if that's possible I would imagine it would require you to have iCloud Music Library, which requires either an iTunes Match or Apple Music subscription.  But you wouldn't be able to sync music to your iPod thorough a Chromebook.  That requires iTunes to be installed on the system, and that's only available for Windows and Mac.  But if you have an iPod touch, then if your music library is in the cloud thanks to iCloud Music Library, you wouldn't have to sync it with a PC in the first place.  It would just update over WiFi, and you'd stream your music from the cloud.  You would also be able to download specific albums/artists/songs to your iPod in order to have them available for offline playing.

If the application supports Offline Mode, then yes you can use it offline.  Gmail and Google Docs/Drive support offline mode, so they would be usable in the situation you describe.

Google Docs has Google's equivalents of Word, Excel, and PowerPoint.  They can open MS Office file formats and save documents in MS Office file formats, and they're free for anyone with a Google account.  However, if your documents have complex formatting, these conversions when opening and saving between formats might not work perfectly.  In that case, you'd want to have an Office 365 subscription, which will allow you to use Office Web Apps.  Those are the browser-based versions of the real MS Office apps.

In terms of pros and cons, the pros are that Chromebooks tend to be highly portable, have good battery life, and represent a solid value proposition.  But more importantly, the main pro of using Chrome OS itself as opposed to Windows and macOS is that you get an environment that's a lot simpler to deal with.  You don't have to deal with tons of app and OS updates all the time, you won't have nearly as much troubleshooting to do, and there's just a lot less risk of things going wrong in general, either in terms of compatibility/interoperability or malware.  It pretty much just works.  In terms of cons, that same simplicity that makes Chrome OS so reliable, easy to use, and hassle-free is also the source of its constraints.  You can't use popular Windows or macOS applications; you're limited to whatever is available for Chrome OS, which basically means browser-based applications and Chrome browser plugins.  In fairness, there are some very impressive browser-based applications and plugins these days, so you can get a lot done in a browser -- that's what makes Chrome OS a viable market offering to begin with -- but if you find that you'd want to use some application that exists on Windows, you can't just install it like you can on a normal laptop.  The other con is that sometimes the value proposition of Chromebooks is taken a bit too far.  If you're coming from a proper laptop to a $200 Chromebook, don't expect the same hardware quality at all.  The cheap Chromebooks have small and/or cheap displays (low brightness and color coverage), cheap keyboards, cheap plastic, and pretty limited CPU and memory specs that can become an issue if you tend to keep lots of tabs open.  There are some nice Chromebooks in terms of build quality and hardware specs, but they're in the $500-600 range -- but at that point you're at or near the cost territory of low-end "regular" laptops.