Depends on what you are riding, for me I ride a 600 E-tec and am just fine.
To me the biggest concern is riding from Grand Marais to Paradise, make sure to get gas in Grand Marais to assure enought to get to Paradise as you are very remote there. Same is true on the way back, fill up in Paradise.
My experience with Pine Stump during the week is, you never know how late they will be there. I've ridden up there about 8pm and they were closed. I think they advertise 10 or 11pm.
One think I've learned in the past is have there phone numbers with you and if you are worried call them early and ask them. Most times if you can give them a time frame they will stay until you can get there!