CHIRP

I have tried and reproduced this issue using a different V82 and using the daily build as well.

Icom radios are a bit finicky with Chirp. They currently don't work well with FTDI.
MacOS is a bit finicky with USB to Serial chips. It more or less likes only FTDI.
So, you're in a catch-22 situation.

Please check whether one of these documents help:
CableGuide
CableGuide FTDI OEM Cables
[RTSystemsCablesAndMavericks]
If there's no solution to be found in any of them, please read: How To Report Issues and provide a debug log. Thank you!
Windows notes: If you are using a generic cable with a Prolific chip, you will very likely need to downgrade your driver to version 3.2.0.0.
It can be found at http://www.miklor.com/COM/UV_Drivers.php
MacOS notes: this OS is apparently very picky about USB to Serial cables. From what I heard, only (genuine) FTDI-based cables can be made work.
You must have the KK7DS Python runtime for Mac OSX installed.
Also see MacOS Tips!
Linux notes: Linux generally is quite good with USB to Serial converter drivers. The most likely cause for grief is a connector which doesn't provide good electrical contact.
Bluetooth notes: connections often suffer from timing issues, please try a cable instead.

Hello, I'm sorry, I though I had updated this thread. I seem to have tracked down part of the problem at least. I recently tried programming my icoms again on a windows computer and ran into the same issue once again. It turned out that it was due to the radios were the European version. So the firmware is different and will not match any sanity checks the code would be running. If I ensured that it was the American version it worked fine, but the European versions (I have 2 of each) were exhibiting the same issue.
My guess it has to do with the different feature sets on the two radios(European doesn't have the NOAA, and uses a different frequency range) if you have any tools or methods for burning the fw bin I'd be happy to send you the bin for the European version when I get back home again. Or you may already have it, not sure.
At any rate CHIRP works great for all my other radios and the American Icoms.

Thanks!
Jesse

Ah, thanks for the feedback! The European radios probably can be made work with relative ease. First thing you should do is to capture a debug log (and you did that already - thanks) as described in How To Report Issues. The second is to provide an image of the radio in question.