Glenn,
Hardest side for the header bolts is the driver side. As Will stated Just have to fiddle with them. I just set the engine and install the headers. Bottom bolt of seven should be in the header before you put it up to the head. Get all the bottom bolts in and the slide the gasket in place. If you gasket is not slotted for the bottom bolts then I would cut them.
Never tried putting the headers on while it was hanging. I just wouldn't trust the hoist. Plus you will risk scratching and gouging the foot boxes with the header bolts.
I wear a size 14 ring and my arms are not the smallest and I can put the headers on with the engine set in place so I think most people can.
Passenger side leave the starter off until you have the header on. Makes it easier.
I also recommend the copper header gaskets and copper permatex sealer. I have had great luck with them.
A small 7/16" combo wrench works nice.
Tony
Unique 427 #4279480 Precision Engine Machine Company 427 s/o 483.47 stroker close ratio toploader 3.31 jag rear