I haven't been on here in a long time but I removed my doors and had the hinges drilled out to put some quick release pins in them for easy on off access.
I have a 92'LE with no PW/PL so my truck was a piece of cake. First, just remove your mirrors. Second, Remove the bolts that connect the door to the hinge. Third, remove the hinge from the truck. If you have a drill press you can drill out the hinge pin, it has a weld on one end of it. If not take it to a metal shop and they will do it cheap. Fortunately for me my neighbor runs a shop out of his garage. Then order some quick release hinge pins off McMaster Carr and reinstall everything. It is very easy to do. As for the connects for the door, I've got nothing for you other than what Freeze said by making the whole bigger in the door. You could cut each wire in the door and put quick connects on each wire so you just unplug each wire individually before the connector.
Driving with the doors off is amazing. Just need to get some military mirrors, or just turn your head since you will have no blindspot. Great when you don't have AC and you live in Florida but sucks when it rains because everything gets wet. Marine grade headunit waterproofing all your wiring isn't a bad idea.