Error when trying conf 1:
connect to [AF_INET]188.72.109.130:80 failed, will try again in 5 seconds: connection timed out
Error when trying conf 2:
SIOCADDRT: Network is unreachable
ERROR: Linux route add command failed: external program exited with error status: 7
In both cases, networking issues. In the first, lack of complaint of routing suggests routing may be working, but host is not listening to port 80 for vpn service, or is dropping your packets to it, or there is a firewall/filter between you and the host dropping traffic. In the second case, there is evidence of a routing issue, like network connection through your gateway is down, or issues with routing table.
Next, why are do you have a "push" directing in your client configs? Are you sure you want to do that?
push "dhcp-option DNS 8.8.8.8"
In the second config, what are you trying to do with this?
route-method exe
IIRC, this "route-method" is just for windows, not for linux. If you are using Raspbian to run your OpenVPN client, this probably won't work as expected, and is probably related to the routing issue with the second config.
Next, between the two configs, why are two different host name used?
conf1: it1.purevpn.net (Resolved: 172.111.180.129 178.170.144.84 172.111.181.2 188.72.109.125 172.111.145.130 172.111.137.93 188.72.109.187 104.250.172.222 172.111.137.223 172.111.180.2 188.72.109.61 172.111.145.2 104.250.172.93 188.72.109.253)
conf2: it-po-ovpn-udp.pointtoserver.com (Resolved: 172.111.144.2 46.243.139.5)
They seem unrelated. Are you sure you mean to use it-po-ovpn-udp.pointtoserver.com as your server in your second config?
Are you trying to force a connection to a single IP/host for service out of the many that are returned when looking up it1.purevpn.net ?
Suggesting some changes, combine the configs into one, assuming it-po-ovpn-udp.pointtoserver.com in the second config was meant to be it1.purevpn.net , dropping the push for DNS in client from both, and the windows routing config in the second from a box running Raspbian:
client
dev tun
remote it1.purevpn.net 80 tcp
remote it1.purevpn.net 53 udp
nobind
persist-key
persist-tun
cipher AES-256-CBC
comp-lzo
verb 1
mute 20
float
route-delay 2
auth-user-pass pass.txt
auth-retry interact
ifconfig-nowarn
key-direction 1
<ca>
[chop: replace with encoded ca]
</ca>
<tls-auth>
[chop: replace with encoded tls auth]
</tls-auth>
With the above, it should try the first "remote" and then if that fails, try the next "remote".
Do they (PureVPN) really ask you to use a config without a <cert> or <key> in your client config to validate you are really being you?
In the first case, if that name is correct for their TCP/80-based service that claims to work with OpenVPN, and there are no routing issues, then the next guess would be a filtering device between you and them, dropping packets. Maybe layer-7 filter blocking traffic that does not conform to HTTP when using standard TCP port for HTTP.. There are many possible reasons for traffic to not reach a host on a port.
