I've done essentially your option 2 to make 40 or so 3.5 x 5 prints using 5 x 7 paper. I was using FB paper. I'd expose 5 sheets and keep them in paper safe, then process them one at a time. By the time the first paper gets to the HCA stage, next one goes into the developer.
If I had to make 100 or more, I'll probably make one good print on larger paper with all the adjustments, then take a picture of that print to make duplicate negatives. This way, all the dodging and burning will only have to be done once.
How many do you have to make? How difficult is it to print? Lots of adjustments or just a straight print? RC or FB? Do they have to be perfect?
Whatever you do, make them in small batches. Chemicals do change when you make lots of prints. Also, you wouldn't want some dust landing on your neg in middle of the session and not know it until you are all done. (happened to me more than once!)