Solution round two:
So something about my DreamPi IP address is changing.
For the last few days since "broken" Pi #2 started magically working, I have dialed an IP address into PuTTY that ends in ".66"
Today when I tried to view the failed-again Pi and dialed that same IP address, it wouldn't go anywhere in PuTTY.
When I looked at my connection settings, it had magically changed the DreamPi #2 IP address, and it now ended in ".98".
I was then able to enter the new IP into PuTTY and it found it again.
Just now I tried the Pi #2 again and it still failed to log on.
I then realized I could go into my router settings and it would actually let me change the IP of Pi #2.
I found a drop-down menu of IP's available to select for Pi #2.
I found the original IP that has worked for the last 5 days, and selected that one. I then restarted the Pi, and used the ".66" IP to view the log in PuTTY, and it established a log successfully.
I then went and attempted to connect to PSO servers and it allowed me connection
Somehow, for some reason, my DreamPi's IP addresses are changing by themselves after X days/hours and this is confusing some part of the equation and causing me to lose connect-ability to servers.