We are using brushes for the most part. I don't trust rollers on siding (it is my issue, not the roller's). We painted it in a rush ten years ago. We spent so long scraping the old paint to get down to bare wood on the original part of the house that we ran out of summer. Even worse, on one side of the addition, I assumed the old paint was in better condition than it was and only put on one coat. It faded so bad that the light grey couldn't hide the original white underneath. That is what has really prompted us to repaint.
The addition half of the house is basically three stories in the front, with a hillside that rises alongside the house so that it is only two stories in the back. But, that is the gable/peak side, so trying to paint the peak on a hill three stories up was very hairy. I built a platform to put the ladder on level footing, but it was made of scrap wood and didn't give me much confidence. I will build a better platform this time that will span the whole side of the house.
We dithered on picking a color so long this summer that we are running out of painting weather. I refuse to let that rush me this time. I will get it done, get it done right. I don't want to have to do it again before I can sell it.