When comparing SizeUp vs Cloak, the Slant community recommends Cloak for most people. In the question“What are the best power user tools for macOS?” Cloak is ranked 27th while SizeUp is ranked 57th. The most important reason people chose Cloak is:
SSL pinning protects against some forms of man-in-the-middle attacks that even SSL encrypted traffic is vulnerable to. Not long ago, iOS did not allow for pinning but that may have changed more recently.
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Pros
Pro Keyboard centric
SizeUp has user-configurable keyboard shortcuts for a set of pre-defined actions.
Pro Supports multiple monitors / spaces
Windows can be sent to different monitors and spaces. It can also be aligned as needed.
Pro Simple
SizeUp is easy and simple to use without having to configure.
Pro AppleScript support allows extending functionality
AppleScript permits adding features such as tiling all open windows. Additionally, FastScripts it allows the user to add keyboard shortcuts to AppleScripts.
Pro Menubar dropdown for shortcuts
Learning a bunch of keyboard shortcuts right off the bat may be difficult to remember at first, which is why a menubar shortcut for the app exists with all the shortcuts listed.
Pro Does SSL Pinning on OS X
SSL pinning protects against some forms of man-in-the-middle attacks that even SSL encrypted traffic is vulnerable to. Not long ago, iOS did not allow for pinning but that may have changed more recently.
Pro Responsive developer
The developer of Cloak is extremely responsive to feedback and quick to answer questions or support requests.
Pro Senses Trusted WiFi networks
Cloak can be set to not use the VPN on whitelisted WiFI SSIDs (like home/work).
Pro Unlimited devices (as long as they're OSX/iOS)
Unlimited devices and data per account, so you can connect up the whole family or office on one account if you so choose.
Cons
Con Nag window
If a license is not purchased there is a nag window (which suspends function) that pops up when loading the app (at user login). The nag pop-up is also summoned at certain time intervals and by performing a certain number of commands (manually or by keyboard shortcut).
Con No on-the-fly split screen window settings
Unlike some other tiling window managers, SizeUp has no way to change the size of split screen actions on-the-fly. Any time a user wants to change how much room on the screen a window takes up when using the split screen function, they will need to manually change the settings, which can be time consuming.