Personally, I like to do my proof prints at a softer grade than I think they will print. I develop my negs to print well on grade two paper. I do the proof prints on grade 1 so that I can see everything that is in the negative--detail that may get lost in the final print.
When I move on to making work prints and fine prints, I will start with a contrast grade slightly below where I think it will finally print. For a grade 2 neg, I will start at grade 1 or 1 1/2 to get the exposure set (the highlights) and then begin to adjust contrast. Whether I start at 1 or 1 1/2 depends on the proof sheet image.
My own experience is that it is easy to go up in contrast, but difficult to go down. So, if I start at grade 2, I end up with prints that are too contrasty. If I start softer, I tend to end up with the correct contrast.
The other trick I use is to do a series of work prints "bracketing" what I think will be the final contrast. If in the darkroom, I settle on a grade 2, I will do a print at 1 3/4, 2 1/4 and 2 1/2. I look at these the next day, before starting on the fine print, outside of the darkroom and under varying lighting. Usually one will jump out. Ocassionally I am torn between two, and I will pick the lower contrast one. Then, by looking back at the low contrast print, I compare to see if any important detail was lost in the shadows, so I will know where to start dodging.