Since you said you're pretty new, pardon me if I'm being too basic.

First, the Development Application Installer has to be enabled on your device.  I'm not sure what, if anything, you'd see when connecting to port 8085 if it's not enabled.  If the installer is enabled, you should be able to point a web browser at your Roku's IP address and see the Development Application Installer web page, so you probably want to make sure that's happening before you try debugging.

Second, there aren't really any "logs" to be seen.  You can only debug your own code when it's side-loaded and running, so if you're trying to see the debug of some other channel when it's running, you won't see anything (except past output from the last run of a side-loaded channel).  And, you only see output from print statements and warnings/errors produced by your code.  You should see some basic startup messages when you launch your side-loaded channel, but after those you'll only see warnings/errors and output from print statements.

You say you get a prompt - is it Brightscript Debugger>?  Can you type commands?  Try pressing Ctrl-C (and return).  Try a few commands like help.

Good luck!
-JT