The funny thing about your edit is that I wish the headphone jack was still in the back because I use regular speakers and all my headphones can connect via usb. Now, unless I use a dock (which will probably have to happen anyway eventually, to be fair) I’ll have to plug things in the front and back at all times.
Mine so far has had no issues like this. I have one monitor connected straight into the HDMI port and another monitor via a Dell dock (from work).