Risk vs Reward: Head to stand in dark / light?

I like to get into my stand well before dawn to settle in,have a coffee and wait for the woods to wake up.

It depends on the specific stand for me. Some spots I can get to quite easily in the dark without making a lot of noise due to the type of terrain. These are the stands that I will use for an early morning hunt, in which case, I like to be set up an hour before sunrise, or 1/2 hour before legal light.
Other stands, I've learned through trial and error, are impossible to reach without making a ton of noise under certain conditions. These are located in hardwood bushes, so when it is very dry or things are frozen before snow covers the ground, I don't bother going in in the dark. If it's warm and the leaves are wet, I can make it in before light.
Often, I will stop at a stand that I can get to easily in the dark, hunt for a while, then still hunt to the other stands that I can't easily reach in the dark.

I consistently have deer in the field when I walk in so I generally walk in and get to stand in low light about 15 minutes before shooting hours. I can somewhat see the outline of deer and try to avoid bumping them headed to stand.

Depends on the stand. If its just a travel route stand then going in at dark is less of a risk. Prefer going in after the sun is up for most stands. I arrowed my best deer halfway to the stand I was walking to, never would have happened if I went in at dark.

i love the sound of the woods coming to life, but hate the feeling of twigs hitting my face when i cant see them.

I'm a pre dawn guy. There was this one year I got in and as I was sorting out my stuff a deer came in under the tree and man did it start to blow, and blow and blow. Dead calm frosty morning and that undeniable sound was just being broadcast over the whole country side, it wouldn't shut up about it. I thought my hunt was ruined after 5 solid minutes of mr. or Mrs. Big nose blasting away but not 20 min later at first legal here comes an oblivious 8pt making a rub line. 15 minutes after him, here comes a dark antlered 10. You just never know how things will play out.

I hunt travel areas/ funnels and like to walk in in the dark. I find that the mornings that I bump deer on the way in tend to be the days that I see the most activity overall.

I walk in 30 mins prior to legal shooting time and on the odd time, I do bump the odd one. I'm thinking if I go in at legal time or day light, I'll get the same result. At least in the dark, I'll let the animal run off, then head for the stand, wait for legal time and try calling. It's worked for me a couple of times.

I like to head to my stand under darkness. I've found that a deer bumped under darkness won't go far and you may get a shot at later, while a deer bumped in the daylight is gone. Just my findings, I'm no expert. Haha

If you head in early be careful. Yes you may spook/bump deer but most of the time they don't know what you are. I've spooked deer sneaking across an open field in pitch black and sat and waited for them to return-they did 15-20 min later.