Remember, it's not 400 feet, it's 640 feet (let's say 650 after trimming). That's $600 for coax _alone_ and you're still going to have over 40 dB of attenuation at 860. Vote "no go".
Got 2k to spend? try this.
Figure out a way to get 120v power to the top of the tower safely and in accordance with building codes.
Put an Icom PCR1500, a laptop computer and an 802.11 wireless access card in a weatherproof box (edit: and I mean WEATHERPROOF), mount it all at the top of the tower and put a discone on top of the tower, connected to the radio.
Use Microsoft Remote Desktop (included with Windows) to access the laptop. Remote Desktop will stream audio to your PC in the shack and will let you view/control the laptop. (and thus, the receiver).
You'll hear _everything_.