Not looking for a flame war here. Just trying to provide all the info necessary to ask for help on a forum.
In my OP I wrote, "I didn't want to list out all the different configs I've tried since there were too many failed attempts to list here."
That line
push "redirect-gateway def1"
is in just about every post out there, including, yes, the HOWTO doc you linked (and I read).
When I add that line to the server config all Internet traffic dies. I cannot ping anything outside my LAN. Here's the log from Tunnelblick after modifying the server config with the redirect-gateway line.
2016-04-18 18:14:41 *Tunnelblick: Established communication with OpenVPN
2016-04-18 18:14:41 OpenVPN 2.3.10 x86_64-apple-darwin [SSL (OpenSSL)] [LZO] [PKCS11] [MH] [IPv6] built on Mar 19 2016
2016-04-18 18:14:41 library versions: OpenSSL 1.0.2g 1 Mar 2016, LZO 2.09
2016-04-18 18:14:41 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:1337
2016-04-18 18:14:41 Need hold release from management interface, waiting...
2016-04-18 18:14:41 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:1337
2016-04-18 18:14:41 MANAGEMENT: CMD 'pid'
2016-04-18 18:14:41 MANAGEMENT: CMD 'state on'
2016-04-18 18:14:41 MANAGEMENT: CMD 'state'
2016-04-18 18:14:41 MANAGEMENT: CMD 'bytecount 1'
2016-04-18 18:14:41 MANAGEMENT: CMD 'hold release'
2016-04-18 18:14:41 Socket Buffers: R=[196724->196724] S=[9216->9216]
2016-04-18 18:14:41 MANAGEMENT: >STATE:1461024881,RESOLVE,,,
2016-04-18 18:14:41 *Tunnelblick: openvpnstart starting OpenVPN
2016-04-18 18:14:42 UDPv4 link local (bound): [undef]
2016-04-18 18:14:42 UDPv4 link remote: [AF_INET]*.*.*.*:1194
2016-04-18 18:14:42 MANAGEMENT: >STATE:1461024882,WAIT,,,
2016-04-18 18:14:42 MANAGEMENT: >STATE:1461024882,AUTH,,,
2016-04-18 18:14:42 TLS: Initial packet from [AF_INET]*.*.*.*:1194, sid=8e085cfc 49cfd652
2016-04-18 18:14:42 VERIFY OK: depth=1, C=US, ST=CA, L=SanFrancisco, O=Fort-Funston, OU=MyOrganizationalUnit, CN=OpenVPN-CA, name=EasyRSA, emailAddress=me@myhost.mydomain
2016-04-18 18:14:42 Validating certificate key usage
2016-04-18 18:14:42 ++ Certificate has key usage 00a0, expects 00a0
2016-04-18 18:14:42 VERIFY KU OK
2016-04-18 18:14:42 Validating certificate extended key usage
2016-04-18 18:14:42 ++ Certificate has EKU (str) TLS Web Server Authentication, expects TLS Web Server Authentication
2016-04-18 18:14:42 VERIFY EKU OK
2016-04-18 18:14:42 VERIFY OK: depth=0, C=US, ST=CA, L=SanFrancisco, O=Fort-Funston, OU=MyOrganizationalUnit, CN=server, name=EasyRSA, emailAddress=me@myhost.mydomain
2016-04-18 18:14:43 Data Channel Encrypt: Cipher 'BF-CBC' initialized with 128 bit key
2016-04-18 18:14:43 Data Channel Encrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
2016-04-18 18:14:43 Data Channel Decrypt: Cipher 'BF-CBC' initialized with 128 bit key
2016-04-18 18:14:43 Data Channel Decrypt: Using 160 bit message hash 'SHA1' for HMAC authentication
2016-04-18 18:14:43 Control Channel: TLSv1, cipher TLSv1/SSLv3 DHE-RSA-AES256-SHA, 2048 bit RSA
2016-04-18 18:14:43 [server] Peer Connection Initiated with [AF_INET]*.*.*.*:1194
2016-04-18 18:14:44 MANAGEMENT: >STATE:1461024884,GET_CONFIG,,,
2016-04-18 18:14:45 SENT CONTROL [server]: 'PUSH_REQUEST' (status=1)
2016-04-18 18:14:45 PUSH: Received control message: 'PUSH_REPLY,redirect-gateway def1,route-gateway 10.0.2.8,ping 10,ping-restart 120,ifconfig 10.0.2.100 255.255.255.0'
2016-04-18 18:14:45 OPTIONS IMPORT: timers and/or timeouts modified
2016-04-18 18:14:45 OPTIONS IMPORT: --ifconfig/up options modified
2016-04-18 18:14:45 OPTIONS IMPORT: route options modified
2016-04-18 18:14:45 OPTIONS IMPORT: route-related options modified
2016-04-18 18:14:45 TUN/TAP device /dev/tap0 opened
2016-04-18 18:14:45 do_ifconfig, tt->ipv6=0, tt->did_ifconfig_ipv6_setup=0
2016-04-18 18:14:45 MANAGEMENT: >STATE:1461024885,ASSIGN_IP,,10.0.2.100,
2016-04-18 18:14:45 /sbin/ifconfig tap0 delete
ifconfig: ioctl (SIOCDIFADDR): Can't assign requested address
2016-04-18 18:14:45 NOTE: Tried to delete pre-existing tun/tap instance -- No Problem if failure
2016-04-18 18:14:45 /sbin/ifconfig tap0 10.0.2.100 netmask 255.255.255.0 mtu 1500 up
2016-04-18 18:14:45 /sbin/route add -net *.*.*.* 10.0.1.1 255.255.255.255
add net *.*.*.*: gateway 10.0.1.1
2016-04-18 18:14:45 /sbin/route add -net 0.0.0.0 10.0.2.8 128.0.0.0
2016-04-18 18:14:45 *Tunnelblick: No 'connected.sh' script to execute
add net 0.0.0.0: gateway 10.0.2.8
2016-04-18 18:14:45 /sbin/route add -net 128.0.0.0 10.0.2.8 128.0.0.0
add net 128.0.0.0: gateway 10.0.2.8
2016-04-18 18:14:45 Initialization Sequence Completed
2016-04-18 18:14:45 MANAGEMENT: >STATE:1461024885,CONNECTED,SUCCESS,10.0.2.100,*.*.*.*
2016-04-18 18:15:26 *Tunnelblick: After 30.0 seconds, gave up trying to fetch IP address information using the ipInfo host's name after connecting.