Meansam,
First thing to do is slam you hand in the door ..... this will put you in the mood for tackling this job!
I personally have done this type of work since 1975, and still do this today. www.aglassenterprise.com Red58 is very close on this experience on this installation. The gasket needs to go on the glass before installation. Make sure to center the gasket on the glass correctly ( vulcanized butt-joint on gasket at bottom center of windshield). Using blue painters tape, secure the gasket about every 12" around the entire gasket. Your tape should go from the outside of the windshield around the gasket to the inside of the windshield. Starting at the BOTTOM center of the windsield insert a 1/4" NYLON rope into the gasket around the entire perimeter of the windshield where the gasket fits onto the pinchweld. Cross the rope approx.6" over the starting point at the bottom. You will have to momentarly pull the tape back from the inside of the windshield to run the rope by, then pull tape back to inside once you have run the rope past each piece of tape. You can now CENTER the windshield into the opening. If you do not have suction cups, and 2 other people you are in for a fight!. The correct tools like, suction cups, hook tool, plastic stick, extra hands, and experience are going to make this job a lot easier. The new gasket is a royal pain in the --- if you have never tried this and personally and 1955 - 1965 car or truck is really the wrong year to be trying this by yourself ..... get someone locally to help, and someone that has done this before, or you will be buying another windshield and gasket once you have broken the windshield, or torn the gasket. Not always poor parts, just the correct no how. You can call me at my shop toll free in the U.S. at 1-800-223-1141 and I will be glad to help you in anyway possible. I do have gaskets, sealants, clips etc. if needed.