Dylan you have actually resolved my original issue for me with your answer. I can expand on your solution after further experimenting.
My issue: One solution containing two projects, a Net Core Web API and Blazor Server Client. At one point when I debugged my solution with both apps starting, a console window would open allowing me to write debug messages from my server client to it. After a Windows Insider update and new VS builds I could not replicate my previous experience and I have seen numerous cries for help on the same issue online.
The fix care of Dylan: The project inside your solution that you wish to have an accompanying console window for should be run as shown in Dylan's screenshot above. This will invariably open a console output window. It appears that so long as you do this the first time, you can then set your multiple projects to start up and the console window will load for the desired project or remain open from the previous debug and continue on.
Note: I have not tested this across multiple projects but have replicated my description above several times after rebooting.