Thanks for the advice Jonathon. I tried logging the output and it became clear that it kept hitting the timeout no matter how high I set the timeout configuration (I went up to 5 minutes). I'm going to see if going up in time helps however it doesn't seem to make a difference so I'm not hopeful on that front.
Since I got home and connected to wifi I upgraded my kernel and ran a package update. I'm hopping something in there solved this problem but I haven't had the chance to test it out and probably won't until tomorrow or Friday. The network manager version number changed so if it's a bug it might have been fixed.
If that didn't change anything I'm not really sure what the next step should be I've been reading the man pages for the NetworkManager and there's lots of configuration settings I could mess around so I might try that.
Now running :
Kernel : x86_64 Linux 4.17.0-2-MANJARO
NetworkManager : 1.10.10-1, Arch Linux
Here's the latest log before I ran an update :
NetworkManager --debug
<info> [1530720148.9636] NetworkManager (version 1.10.8-1, Arch Linux) is starting... (after a restart)
<info> [1530720148.9637] Read config: /etc/NetworkManager/NetworkManager.conf (lib: 20-connectivity.conf) (etc: network.conf)
<info> [1530720148.9680] manager[0x5597620df080]: monitoring kernel firmware directory '/usr/lib/firmware'.
<info> [1530720149.2104] hostname: hostname: using hostnamed
<info> [1530720149.2104] hostname: hostname changed from (none) to "Marsha-P-Johnson"
<info> [1530720149.2106] dns-mgr[0x5597620f9930]: init: dns=default, rc-manager=symlink
<info> [1530720149.2118] rfkill1: found WiFi radio killswitch (at /sys/devices/pci0000:00/0000:00:1c.2/0000:03:00.0/ieee80211/phy0/rfkill1) (driver wl)
<info> [1530720149.2120] rfkill3: found WiFi radio killswitch (at /sys/devices/platform/dell-laptop/rfkill/rfkill3) (platform driver dell-laptop)
<info> [1530720149.2272] manager[0x5597620df080]: rfkill: WiFi hardware radio set enabled
<info> [1530720149.2272] manager[0x5597620df080]: rfkill: WWAN hardware radio set enabled
<info> [1530720149.2297] settings: loaded plugin keyfile: (c) 2007 - 2016 Red Hat, Inc. To report bugs please use the NetworkManager mailing list.
<info> [1530720149.2299] settings: loaded plugin iBFT: (c) 2014 Red Hat, Inc. To report bugs please use the NetworkManager mailing list. (/usr/lib/NetworkManager/libnm-settings-plugin-ibft.so)
<info> [1530720149.2381] keyfile: new connection /etc/NetworkManager/system-connections/Algiers (472513c3-47e1-4921-b250-17c337373816,"Algiers")
<info> [1530720149.2449] keyfile: new connection /etc/NetworkManager/system-connections/AlleyCat (a01d385d-ee56-4710-ae25-ea6570a961fc,"AlleyCat")
<info> [1530720149.2516] keyfile: new connection /etc/NetworkManager/system-connections/GRAHAM31_5 (51f9c225-4ff4-427f-859f-c428c90b30cf,"GRAHAM31_5")
<info> [1530720149.2581] keyfile: new connection /etc/NetworkManager/system-connections/GRAHAM31 (3e3e8e62-e00b-4063-ae96-a1f113df2512,"GRAHAM31")
<info> [1530720149.2595] manager: rfkill: WiFi enabled by radio killswitch; enabled by state file
<info> [1530720149.2595] manager: rfkill: WWAN enabled by radio killswitch; enabled by state file
<info> [1530720149.2596] manager: Networking is enabled by state file
<info> [1530720149.2597] dhcp-init: Using DHCP client 'internal'
<info> [1530720149.2597] Loaded device plugin: NMBondDeviceFactory (internal)
<info> [1530720149.2597] Loaded device plugin: NMBridgeDeviceFactory (internal)
<info> [1530720149.2598] Loaded device plugin: NMDummyDeviceFactory (internal)
<info> [1530720149.2598] Loaded device plugin: NMEthernetDeviceFactory (internal)
<info> [1530720149.2598] Loaded device plugin: NMInfinibandDeviceFactory (internal)
<info> [1530720149.2598] Loaded device plugin: NMIPTunnelDeviceFactory (internal)
<info> [1530720149.2598] Loaded device plugin: NMMacsecDeviceFactory (internal)
<info> [1530720149.2599] Loaded device plugin: NMMacvlanDeviceFactory (internal)
<info> [1530720149.2599] Loaded device plugin: NMPppDeviceFactory (internal)
<info> [1530720149.2599] Loaded device plugin: NMTunDeviceFactory (internal)
<info> [1530720149.2599] Loaded device plugin: NMVethDeviceFactory (internal)
<info> [1530720149.2600] Loaded device plugin: NMVlanDeviceFactory (internal)
<info> [1530720149.2600] Loaded device plugin: NMVxlanDeviceFactory (internal)
<info> [1530720149.2610] Loaded device plugin: NMWwanFactory (/usr/lib/NetworkManager/libnm-device-plugin-wwan.so)
<info> [1530720149.2611] Loaded device plugin: NMWifiFactory (/usr/lib/NetworkManager/libnm-device-plugin-wifi.so)
<info> [1530720149.2644] Loaded device plugin: NMTeamFactory (/usr/lib/NetworkManager/libnm-device-plugin-team.so)
<info> [1530720149.2646] Loaded device plugin: NMOvsFactory (/usr/lib/NetworkManager/libnm-device-plugin-ovs.so)
<info> [1530720149.2649] Loaded device plugin: NMBluezManager (/usr/lib/NetworkManager/libnm-device-plugin-bluetooth.so)
<info> [1530720149.2652] Loaded device plugin: NMAtmManager (/usr/lib/NetworkManager/libnm-device-plugin-adsl.so)
<info> [1530720149.2658] device (lo): carrier: link connected
<info> [1530720149.2662] manager: (lo): new Generic device (/org/freedesktop/NetworkManager/Devices/1)
<info> [1530720149.2670] manager: (eno1): new Ethernet device (/org/freedesktop/NetworkManager/Devices/2)
<info> [1530720149.2679] keyfile: add connection in-memory (71ceed48-9a3f-361f-9f3d-26043deeddcb,"Wired connection 1")
<info> [1530720149.2683] settings: (eno1): created default wired connection 'Wired connection 1'
<info> [1530720149.2691] device (eno1): state change: unmanaged -> unavailable (reason 'managed', sys-iface-state: 'external')
<info> [1530720149.2702] wifi-nl80211: (wlp3s0): using nl80211 for WiFi device control
<info> [1530720149.2712] manager: (wlp3s0): new 802.11 WiFi device (/org/freedesktop/NetworkManager/Devices/3)
<info> [1530720149.2720] device (wlp3s0): state change: unmanaged -> unavailable (reason 'managed', sys-iface-state: 'external')
<info> [1530720149.2727] device (wlp3s0): set-hw-addr: set MAC address to 96:90:22:B2:76:10 (scanning)
<info> [1530720149.2751] ovsdb: Could not connect: No such file or directory
<info> [1530720149.2771] bluez: use BlueZ version 5
<info> [1530720149.2773] modem-manager: ModemManager available
<info> [1530720149.2779] supplicant: wpa_supplicant running
<info> [1530720149.2779] device (wlp3s0): supplicant interface state: init -> starting
<info> [1530720149.2789] bluez5: NAP: added interface D0:53:49:D7:AE:02
<info> [1530720149.3367] sup-iface[0x559762090970,wlp3s0]: supports 1 scan SSIDs
<info> [1530720149.3373] device (wlp3s0): supplicant interface state: starting -> ready
<info> [1530720149.3374] device (wlp3s0): state change: unavailable -> disconnected (reason 'supplicant-available', sys-iface-state: 'managed')
<info> [1530720155.1946] device (wlp3s0): Activation: starting connection 'AlleyCat' (a01d385d-ee56-4710-ae25-ea6570a961fc)
<info> [1530720155.1947] audit: op="connection-activate" uuid="a01d385d-ee56-4710-ae25-ea6570a961fc" name="AlleyCat" pid=1048 uid=1000 result="success"
<info> [1530720155.1951] device (wlp3s0): state change: disconnected -> prepare (reason 'none', sys-iface-state: 'managed')
<info> [1530720155.1953] manager: NetworkManager state is now CONNECTING
<info> [1530720155.1961] device (wlp3s0): set-hw-addr: reset MAC address to D0:53:49:D7:AE:01 (preserve)
<info> [1530720155.2076] device (wlp3s0): state change: prepare -> config (reason 'none', sys-iface-state: 'managed')
<info> [1530720155.2078] device (wlp3s0): Activation: (wifi) connection 'AlleyCat' requires no security. No secrets needed.
<info> [1530720155.2079] Config: added 'ssid' value 'AlleyCat'
<info> [1530720155.2079] Config: added 'scan_ssid' value '1'
<info> [1530720155.2079] Config: added 'bgscan' value 'simple:30:-80:86400'
<info> [1530720155.2079] Config: added 'key_mgmt' value 'NONE'
<info> [1530720155.2372] device (wlp3s0): supplicant interface state: ready -> disconnected
<info> [1530720155.2379] device (wlp3s0): supplicant interface state: disconnected -> inactive
<info> [1530720155.2435] device (wlp3s0): supplicant interface state: inactive -> scanning
<info> [1530720159.4581] device (wlp3s0): supplicant interface state: scanning -> associating
<info> [1530720159.5385] device (wlp3s0): supplicant interface state: associating -> completed
<info> [1530720159.5386] device (wlp3s0): Activation: (wifi) Stage 2 of 5 (Device Configure) successful. Connected to wireless network 'AlleyCat'.
<info> [1530720159.5396] device (wlp3s0): state change: config -> ip-config (reason 'none', sys-iface-state: 'managed')
<info> [1530720159.5401] dhcp4 (wlp3s0): activation: beginning transaction (timeout in 300 seconds)
<warn> [1530720459.6508] dhcp4 (wlp3s0): request timed out
<info> [1530720459.6510] dhcp4 (wlp3s0): state changed unknown -> timeout
<info> [1530720459.6829] dhcp4 (wlp3s0): canceled DHCP transaction
<info> [1530720459.6830] dhcp4 (wlp3s0): state changed timeout -> done
<info> [1530720459.6834] device (wlp3s0): state change: ip-config -> failed (reason 'ip-config-unavailable', sys-iface-state: 'managed')
<info> [1530720459.6837] manager: NetworkManager state is now DISCONNECTED
<info> [1530720459.6838] manager: startup complete
<warn> [1530720459.6843] device (wlp3s0): Activation: failed for connection 'AlleyCat'
<info> [1530720459.6852] device (wlp3s0): state change: failed -> disconnected (reason 'none', sys-iface-state: 'managed')
<info> [1530720459.6875] device (wlp3s0): set-hw-addr: set MAC address to CA:8D:83:8D:27:D5 (scanning)
<warn> [1530720459.6888] sup-iface[0x559762090970,wlp3s0]: connection disconnected (reason -3)
<info> [1530720459.6890] device (wlp3s0): supplicant interface state: completed -> disconnected
^C<info> [1530720619.6174] caught SIGINT, shutting down normally.
<info> [1530720619.6209] device (wlp3s0): state change: disconnected -> unmanaged (reason 'unmanaged', sys-iface-state: 'managed')
<info> [1530720619.6212] device (wlp3s0): set-hw-addr: reset MAC address to D0:53:49:D7:AE:01 (unmanage)
<info> [1530720619.6345] exiting (success)