Bizarre WiFi Connectivity Issue; Self-Assigned IPs, Static IP Doesn't work

The short and sweet of the problem: Macs/Apple Devices are pulling self-assigned IP addresses when connecting to a Linksys EA6900/AC1900 router.
Here’s the detail: I am working at an office with 1 Airport Extreme and 1 Linksys EA6900/AC1900, both are configured for Bridge Mode and both use WPA. DHCP is being handled by a Watchguard XTM5 series firewall.
When Macs (and often iPhones) connect to the Linksys (on 2.4 or 5Ghz) they get a self-assigned IP address. If you enter a manual address you still do not have any connectivity. However, if you connect to the Extreme you will instantly get an IP address, and if you switch to the Linksys your DHCP address will carry over and you will retain connectivity. This problem does not happen to the Windows machines in the office- they all connect to all base stations without any issue. Total users on the network range from 5 to 20 WiFi users at any given time plus and AppleTV (also affected).
More info: When there are between 5-10 people in the conference room for a morning meeting the Macs will all revert to self-assigned addresses (even if they were working before). The workaround has been to connect to the Extreme, but there are occasions when this occurs that the Extreme will also not seem to pass the DHCP addresses from the firewall; addresses become self-assigned and you lose all internet. To make matters more odd, this behavior seems to really only affect the network during business hours; after hours the Linksys works pretty much normally and any device can connect without issue.
Things I’ve done: Run Wireshark and located a number of rogue devices that were handing out overlapping DHCP addresses. Identified machines that were ARP storming and removed them. Expanded the DHCP pool so that we aren’t running out of addresses and confirmed that we had enough by checking the logs.
More things I’ve done: Used Netspot to check signal strength and channel overlap and isolation. I have mapped the signal strength by location and we have strong signals to the various locations (the Linksys AP is 7 feet from the conference room). I have checked that the firmware is the most recent version.
I can’t find any logical reason for the Macs (and pretty much only the Macs/Apple devices) to not be picking up DHCP info through the bridge mode devices. I would tell them to get another Extreme but they are going to be deploying a Cisco Meraki system soon and I suspect that this problem will persist since the Linksys was put in place because the last AP displayed the same behavior with the Macs picking up self-assigned IPs. Affected Macs range from 2010 era MBP and Air to 2013 MBP and Air and they are running OSX 10.8 through 10.10.
As for the history of this network, I just walked into this company and know very little about how well it worked before, but apparently it has always been flaky according to the staff.

I agree that something isn't right; I am going to cut over DHCP services from the Watchguard to the newly deployed OS X Server tonight and see  if that changes anything.
On the other hand, faulty DHCP server/client settings doesn't explain why applying a static IP still leaves you with no connectivity. I think that clue is also fairly important but I can't figure out what would be blocking connectivity on a static IP setup.

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    After upgrading to Leopard I keep getting "AirPort has a self-assigned IP address and may not be able to connect to the Internet." when I try to connect to the wireless network. Thus, wifi does not work at all. I've researched it best I can and it seems to be a problem with the router assigning an IP address to the mac, but why didn't this happen in Tiger? However if I play around with it for awhile it will randomly start working, but the same method doesn't fix it everytime. It also works fine in bootcamp. If I physically plug into the router, it works fine. This problem didn't exist in Tiger at all.
    Message was edited by: SuperDupe453

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    We're using Cisco APs, with multiple VLANs & SSIDs. They authenticate, but get automatic self-assigned IP addresses. None of our PC clients are experiencing this issue, nor older 10.4.x OSX clients. This looks like a bug, from what I was able to discover:
    http://forums.macrumors.com/showthread.php?t=384947
    Is Apple aware of this, and/or working on a fix? I've seen many issues over the last year or so with Airport clients and wireless connectivity..

    This is a "user to user" help forum that is designed as a self-help system, independent of Apple's Technical Support system. No one here can say what Apple knows or is doing about a specific issue (pure speculation is discouraged). We share experience and suggest possible solutions or workarounds.
    One way to ensure that your issue is brought to Apple's attention is to use their feedback form for OSX - http://www.apple.com/feedback/macosx.html
    Since the link you posted is from late last year, there have been many updates to Leopard. Some of the updates mention network reliability. Even though Apple has stated that the Pram chips don't control network connections, I have had some luck by Zapping The Pram - http://support.apple.com/kb/HT1379 - Remember to check your System Prefs for things like date/time settings after you Zap.

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