1) I would go before. Removing growth will reduce transpiration and thus stress...if I understand your question correctly.
2) They will strike outdoors. More slowly since you do not have as much control over environment.
3) No feeding of fresh cuttings is needed whatsoever. Once the cuttings strike, begin feeding at full strength.
4) I have never heard of someone doing this. The cutting needs all it's energy for new root growth. There will be no way for the cutting to transport nutrients for flowering without roots.
Do not always assume that transplanting will stress your plants. Mostly, when I transplant, my plants burst with new growth...like taking your boots off after a long day walking - it feels awesome to let your feet breathe.
Transplant stress has a lot to do with the individual plant's genetics IMO...some plants like it, some don't.
EDIT: When striking outdoors, keep them in shade, they will strike faster. Same goes for indoors, don't put them under HID's unless at a significant distance.