At any time, username and password authentication is used, the common wisdom is to protect the transport of this data using encryption (SSL, HTTPS, etc.). But this makes endpoints potentially vulnerable.
Realistically, what is at greater risk of invasion?
Transport layer: Compromised with wireless packet sniffing, malicious listening, etc.
Transport devices: Risks include ISPs and Internet backbones that sniff data.
End user device: Vulnerable to spyware, key loggers, shoulder surfing, etc.
Remote Server:. Many unmanaged vulnerabilities, including malicious operators, hacks that lead to data theft, physically damaging servers, backups stored in insecure places, and much more.
My gut reaction is that while the transport layer is relatively easy to secure with SSL, the risks in other areas are much, much greater, especially at the endpoints. For example, at home, my computer connects directly to my router; from there it goes straight to my Internet service provider routers and to the Internet. I would rate the risks at the transport level (both software and hardware) low to nonexistent. But what is the security for the server I'm connected to? Have they been hacked? Is the operator collecting usernames and passwords, knowing that most people use the same information on other sites? Similarly, was the computer infected with malware? This seems like a much greater risk.
My question is this: should I worry if the service I'm using or developing is not using SSL? Of course, these are low-hanging fruits, but there are much more fruits higher.