This is simple but it works for me…
1.) I use Yummy FTP with a Yummy FTP Alias. The Yummy Alias is a “droplet” that sits on your desktop (or anywhere you want.) Simply drop you image on the Yummy Alias and it uploads to your server to the folder you defined (ie: images, resources, etc). Thus, uploading an image is as easy as dropping it on an icon.
2.) As for the full path url I use a Keyboard Maestro macro. But this could be setup with any number of OSX utilities. I set a Hotkey to enter “https://www.mywebsite.com/images/” then all I need type is the image file name.
At some point I have typically copied the name of the image (in OSX finder), usually when sizing or optimizing the image. Thus, to enter the image name in RW it’s a matter of hitting my Hotkey and then control P for paste.
This works nicely for me, you may not like it. But by using a hotkey in conjunction with copying the filename in the finder and pasting it, I eliminate the frustration of having typed an error when entered into RW.