The whole point of the Chromebook is to be a simple client for web-based services, and Apple’s iCloud site is pretty great. iCloud-wise, you’re stuck using the site, but that’s not as bad as it sounds. If you’re all-in on Google services, and most of your apps are web apps, you should consider a Chromebook.
Although, if you are going to run Windows, and you have a MacBook-size budget, then Microsoft’s own Surface hardware is your best option, because you don’t have to deal with all the crapware loaded on competing Windows laptops. Even the cheaper Surface Laptop 3, which starts at $999, offers a mix of ports - and looks pretty great.