I see some issues on your example images.

1. Use network is off
2. Local PC ip is different than the Select one
3. Remote (dreambox) ip is out of range of the 10.0.0.X network.
4. Based on your screenshots you use at least Windows 7 or higher.

But okay, on this way it will not succeed to flash the box.
The best way is to repair/flash the box with a windows Xp system, or what you also can try is to hold the front push button, switch the box on, hold the front push button until you see the ip on the oled display.

Use this ip in your browser to upload the image file and the boot loader.

Other method if present, same as above but than do it with the push button on the back.
This is a second option.

Needless to say that you need to connect your dreambox on your network and it must be a dhcp network.