I have not done it with the windshield out myself so hopefully others will chime in, but I have replaced the dashpad with the windshield in, and it is a pain in the but to get the screws in that metal trim piece installed. it would be way easier with the windshield out, but I think you would have to have the windshield gasket in at least or the metal trim piece would not fit right I don't think. again I have not tried it myself.
I replaced my dash pad with the windshield out and couldn't imagine doing it any other way. It's really easy when you can lean out through the window opening from the inside to trim the front of the dash and in general, do the fitting. I also did adjustments from the outside of the car leaning in through the dash. It also makes the dash pad trim a lot easier to install. Then, with installing the windshield after that it's a breeze.
I just pulled out my stubby screwdriver to install the pad with the windshield in.
Now I'm about to redo both and the windshield is currently out so I'm interested to see people's opinions.
I replaced my dash pad on my 70 with the windshield in. I did have the steering wheel off for other reasons but I didn't think it was a big deal. There are only a few screws and as I recall, it took less than an hour.
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