To recap what you are saying (correct me if I am mistaken).
Someone runs the TEServer executable file.
Up comes a GUI.
They select some options, profile, password, etc.
Click start server.
I suppose an advanced user could have a file and run the file
TEServer -r someoptions.ini
and have it auto-run?
That sounds good, the GUI should have a button to save a someoptions.ini file so one can use the GUI on the workstation to create a settings-file and then throw it to the server if it is another computer. (but that is just details)
If people who connect don't have the correct profile (for a custom profile) then they will be directed as to where to download it, or the server could send it to them (unless its too big), or just be rejected.
Profile-files would be quite light compared to what the server will got to do when the game starts, so I see no issue with having the server transfer the files. If you by redericting suggest that the client will download the file automatically then I guess it is okay, though I guess downloading from elseware may delay the game for everyone.
_________________My OpenTTD contributions
(AIs, Game Scripts, patches, OpenTTD Auto Updater, and some sprites)Junctioneer
(a traffic intersection simulator)