Syncing files between machines

No. Quicken isn't built to do that. (There was some obscure reference to being able to do this in the release notes about two years ago, but I don't believe it was accurate.) The Quicken Cloud is built to sync between a estop base Quicken Mac or Quicken Windows data file and the mobile app/web interface, but not between two desktop data files. If you try it and it appears to work, I'd be afraid that somewhere down the road you will face corruption issues.

The approved/recommended way to use two Mac is to move the data file between the two computers. And don't move the actual data file; move either a compressed .zip copy of the data file (click the data file in the Finder and select File > Compress) or a backup (.quickenbackup) file between the two machines. Moving the live data file without one of these wrappers will lead to oil corruption/access restriction issues at some time down the road. To move the file back and forth, you can use a flash drive, email it to yourself, use Mac File Sharing, use AirDrop, use Dropbox -- and way you'd move any file between the two computers. 

One safe, fairly simple and semi-automatic way to handle this is to set your automatic backup location to a cloud service (e.g. Dropbox, iCloud Drive, etc.). Do this on both computers. Each time you close Quicken, the latest file will be backed up to the cloud. When you want to work on Quicken on either computer, DO NOT open the local Quicken file. Instead, double click the cloud-stored backup and restore it. You will then be working on the most recent data no matter which computer it was updated on. If you do this, it is important that you make sure you quit Quicken and let the backup proceed each and every time you use it, and never have Quicken open on both computers at the same time.