Ran this as part of a set of back-to-back training runs for a 100M. I did this unsupported and carried all my fuel from the start. Refilled water twice, first at the tap by the lake at Skyline Ridge OSP, and then again at the spigot along the Lost Trail at Windy Hill OSP. Took a few small wrong turns at Upper Stevens Creek and Skyline Ridge but quickly backtracked and funneled my way back onto the route to make sure I completed the full trail. Had great weather the whole way, possibly the last week of "green grass" in the hills. Highly recommend this route, one of the best in the Bay!
I'd recommend to be cautious on the road section between Windy Hill and Woodside, and if doing this in spring/summer, watch out for lots of poison oak on the single-track between Wunderlich and Huddart parks.