Get lost at those places? How can that happen?
I'll put 2 cents in for Tolt as the easiest place not to get lost with a second for East as long as you don't range far up and over the road above Mr. Hill.
Depends on your sense of direction. Some have one, I guess some don't.
Tolt: there are some leftover soup can lid signs from the 42 originally put out there so you may occasionally run into one that may help orient you to which trail you are on or just left. The main road loops around the main part of the lower tree farm section so getting on that and heading East will eventually get you to IAB in some way. There is a new road not on the maps cutting through Blair Witch. Just don't go West on it.
East: If you stay low, you are bordered by a gully, the SVT, and private homes to the East so you can't get lost. Climb Mr. Hill and session that and you hae a reference point as some trails cross it a few times.Explore above it and you will need to watch for the black and white road numbers to guide you most are indeed marked. Like 30130 at the bottom of Safety First. Take the 4th trail from the TH on the SVT quickly up on to an old access road to the power lines and then review the map for where you are. The power lines are a good reference point there.
West: Much bigger acreage and the trails are more spread out. Outback isn't as far "out back" as was thought when built but still hard for some to find. One easy thing to do is keep an eye out for the upper and lower Beaver Ponds for reference points and don't ride East of the power lines unless you want to ride around the back of the 356th homes to the Tokul East trails.
(Not sure a night ride with Charlie would be real good for getting the lay of the land simply because of the darkness. I'm sure he'd show you a great loop though!)
Edit: *chuckle* I guess Hawkwns and I were helping at the same time...
Also, per livinlife, the 39th access to T-West is "okay" if you let the owner know you are going through there or leave a business card in his mailbox or something like that. I still see people riding from teh big lot across from the Fall City Grill. But, far fewer than before that, "issue" came up.
BTW: What? No Bobsled finish after Full Bench?
(Yeah, the lower trails like Monster, Stickerboy, and Bra can be real muddy in winter but probably frozen now.) Black Bear is real good all year around.