Windoze 7 may not like the post box...............
To answer your one question, the side marker lamps DO stay on in both headlight positions. Your problem might be the bulb, but it could be the receptacle.On my 68, the side marker receptacle is original and the springload is not enough to contact the bottom of the bulb and maintain the circuit. One fix I've tried before is to add a bit of solder to the contact points on the bulb; in my case, the bulbs then became so difficult to put into the receptacle (tight quarters, there) that I couldn't get it to work. You might have better luck with this than I did. As for me, I think I need a new receptacle assembly.Hope this .02 helps.
You can stretch the springs a bit to increase the tension on the bulb base. I have used that process several times.