Trying to understand ping
0 and 255 are not valid addresses to have machine at on a 255.255.255.0 subnet network.
255 is the "broadcast" address an 0 is the "network address.
Related reading Why can't IP addresses start with 0 or 255?. The answer addresses the broad case of the wide IP addresses, but the rule apply to subnetted addresses as well so for a 255.255.255.0 subnet the first and last IPs are reserved.
Regarding the pinging of .253... in your first ping it is essentially asking every network adaptor it has if it has a route to the host.
In two of the cases they have replied Destination host unreachable. which is essentially saying "if it was here then we'd let you know, but it is unreachable for some reason"
The weirder one is the VPN network gateway which instead says Destination net unreachable. in this case it is saying that due to subnetting and other factors is has absolutely no way it can talk to any machine over on that network.
Your final ping looks like what I would expect to see. Your local network adaptor is just telling you the address is unreachable.