Hi Aaron,
You are a lifesaver! Thank you so much!
Now that I am past that point, I put together a simple page and tried to run debugging to see if it works.
I did so by clicking on the bug button next to the play button. I get the following message.

RDS on the server is turned on and I have triple confirmed the password. Just in case I made the same mistake multiple times (unlikely), I also tried the credentials for "admin" with the same result.

Thanks Aaron & Adam,
JT
jvc714 wrote: 
RDS on the server is turned on and I have triple confirmed the password. |
Hi jvc714,
There is more than one thing we can try. First, here's a step I've found I must do 100% of the time after a fresh install of CF:
1) In CF Admin > Debugger Settings, uncheck (disable) the "Allow Line Debugging" option and click "Submit Changes"
2) Then check (enable) the "Allow Line Debugging" option and click "Submit Changes"
3) Restart CF
4) Test Debugger in CFB again (Window > Preferences > Adobe > RDS Configuration > "Test Debugger" and "Test Connection" buttons
Please let us know the result of clicking those 2 buttons.
There may also be a port issue. There are two ports: A "Debugger Port" and a "Debugger Server Port". The 1st is configurable via CF Admin > Debugging and Logging > Debugger Settings. The 2nd is random by default unless forced via a JVM switch at CF Admin > Java and JVM > JVM Arguments and then add this JVM arg if necessary: -DDEBUGGER_SERVER_PORT=X (where X represents the fixed Debugger Server Port you'd like CF/CFB to use) and then restart CF.
GTG for now, hope that helps!,
-Aaron