I went with the USB/Ethernet/Bluetooth printer and a printer Driven Cash Drawer.

Here was my thinking:

I found that the Square Stand has 3 USB ports.  1 is taken by the Stand, 1 for a printer and one for the cash drawer, now you have 0 for a USB Scanner or anything else you may need to add by USB in the future.

The USB/Bluetooth/Network printer is able to control a cash Drawer.  With it being Network capable I can use 2 Stands, to control 1 Receipt Printer and 1 Cash Drawer.  I also found out that my Android when connected to the WiFi network can also connect to the Network printer and the Cash Drawer.  The problem with this is you can have multiple Checkouts using 1 Cash Drawer or 1 Printer, and the reports can be confusing.  The other thing is proximity of multiple devices using 1 Printer and 1 Cash Drawer, mine are setup across from each other that we can just reach down or turn around to grab the printed receipt or get into the cash drawer.  The printer with the most types of connections is also in my opinion future proofing for different types of connections. 

the USB Cash Drawer and Printer are easier to setup and you do not have to worry about devices being assigned the same IP address.  Some Network Devices have their setting set to give a Static IP address instead of getting one from your Router.  I have had this issue with a Network Desktop Printer and a Network Security Camera.  I then had to troubleshoot which camera it was and which Printer it was and reassign the IP addresses.  You would not have this with a USB device.  

With USB and Bluetooth only 1 device can connect to a receipt printer at a time, as far as I know.  I have not tried connecting these as a USB printer on a Router with a USB port to confirm this would work.