WinSCP always show the same amount of stars/dots (16), when not in editing mode.
Did you actually test a login with the modified password?
I'm running version 5.9.3 of WinSCP on a Windows 10 machine. I'm logging into a server using the SFTP protocol.
I frequently use WinSCP to log in to a particular server. This morning I had to change the password on my server account. I edited the WinSCP site password, but when I saved the site or even saved it as a different site, the password seems to revert back to the old password (judging by the length of the password). Even creating a new site for the same server seems to want to use the old password.