Difficult question. I usually tip a tow boat or shuttle driver - $5-10/person, although have not towed for 5+ years. Otherwise, I'm dealing with an owner and it seems awkward to tip an owner, especially since some (many? just mine?) have added an "outfitting" charge, like  5% of the total. I don't mind that at all, but not sure I should add.

I tip the tow boat operator $10 or so. Other than a tow I don't use an outfitter.

I will tip the tow boat driver besides the server if I get a meal.  I usually have good conversations with the boat driver to Prairie Portage.  Last September on my solo I gave an older driver a $20.  Made both him and me feel good.

Depends on the service. I've had one tow from Black Robe that almost refused to swing by the Lac La Croix pictos for my friends who had't gotten a good look at them. It was too windy on the way into Bottle to hold the boat, it was, but different driver then. The snooty driver also threw my graphite paddles around like they were plastic beaters. He was real careful of my ugly sticks  , thought he had that backwards  . Then he stuck his hand out like the tip was expected. One person in our group did tip him, but I wouldn't have.

I think I got off on the wrong foot with this Crane Lake outfitter, I didn't know why at the time. In our introduction conversation I mentioned mostly getting towed in from the Indian Village by a certain 1st nation character (yes Jimbo, same guy). I knew my contact at the village was a lot cheaper, and thought to myself the boat looked familiar too. If you remember there was a time when Cdn outfitters could get you cheaper permit rates if you used them. I'm guessing using my contact in the village qualified the US outfitter as Cdn even though he was based in Crane Lake. I could tell this guy's jaw tightened a bit when I told him how I got towed in, but I thought it was just that I used someone else. Took me awhile to figure out the whole story.

I have had great service, and do tip then, especially if it means getting on fish.

Jimbo I thought you'd like this story. He's a slick one  ,, no names