I use Dropbox but it hurts every time!

Hey Eric! If you use GDrive correctly everything should run really smoothly! I basically have all my documents in the cloud. Plus it has the benefits of eliminating potential risks with hardware problems.

For licenses you have to pay a little more if you want "more seats" but it depends of the software you use.

Licences

I avoid software that only allows use on 1 computer. Thankfully, most allows at least 2 (Adobe, Sketch, Affinity etc all allow use on at least two computers).

File sync and project management

I use Git/GitHub/Git Tower for a lot of projects, especially for final production assets and web stuff. I use Dropbox for things that don’t make sense to store on GitHub. I’ve tried using iCloud Drive a few times and I keep catching it not syncing properly. I’ve been burned by it enough that I think I am completely done with it.

I’m not a fan of storing files on non-generalised cloud storage, because that means you often don’t have easy access to bulk download or backup those files, and it often means the storage is tied to the tool.

I’m a huge dropbox fan. As a designer and sometimes photographer my entire projects library as well as my Lightroom catalog are in Dropbox. That way, no matter which mac I use, all my files are available.

I'd say it depends on the purpose of having multiple computers. If one is for work and another is personal – the shared Dropbox folder with work stuff should be sufficient enough. Personally, I use iCloud for file sync simply because of ecosystem benefits on other Apple devices I have.

There is another amazing way to sync design files (if you design in Sketch or XD) – (Abstract)[https://www.abstract.com]. So all your design files are stored in the cloud and under version control.

For syncing apps can definitely recommend (Setapp)[http://setapp.com/]. You just have one account with apps connected to it. Once you sign in on another machine all those applications you have installed will be also installed on another machine. Very convenient.

Yes, you won't be able to find Sketch in Setapp, for example. But for those kinds of products, it's usually possible to activate single license eon multiple machines.

Hope this helps :)

For my iCloud, the most easy and thenbest way, its cheap and works amazing, all my important document its here and the recents project, about licenses if you buy the app in Apple Store don't have any problem, you can install in all machine you have with you iCloud account.

About buy the software for the officially web page or other way, sometimes and with many app, include the possibility to install in two o three machines.

PD: sorry for my English, I am learning :).

Had bad experience with dropbox on file consistency, and there was some problem with repositories not working on cloud synced folders.