So I'm wondering specifically how people are planning these trips and navigating these hikes above tree line. You can't simply count on it being sunny the whole time so you can see where you are at all times and the winds appear to obliterate even the freshest tracks of previous hikers so you're pretty much on your own the entire time.
1) Do you sketch out the hike on a map with compass bearings, etc? What if you get off your waypoints or pre-planned locations?
2) Are you only taking routes you have done many, many, many times before so you are extremely familiar with them?
I own and know how to use a compass and GPS but I've never really gone out on a hike following a list of bearings. Not something you really need following posted trails.
My season ending goal is to do a "starter" above tree line experience like Pierce-Eisenhower or Madison
I hike in the Northern Presidentials more frequently than other areas of the WMNF. I mostly hike solo. If going above treeline and it's anything but clear, I have a compass in my chest pocket or on a lanyard around my neck. Before I leave the trees, I take a compass bearing on my route and on the return bearing as well. Sometimes, I will do this ahead of time near the warmth of a woodstove with map and compass and keep the bearings on a paper in my pocket with trail distance notes, etc. I memorize the escape route bearing.
I do routes I am unfamiliar with as well as routes I have done multiple times. I treat them fairly equally since even though I may have hiked a route numerous times, it is never under the same conditions, so I try to treat it as a new experience.
I hike frequently and have no issues turning back which I have done several times on Washington, Adams, Madison, Jefferson, Monroe, and even a few times on Mount Nancy, among others. I stay within my comfort zone, which is of course different for everyone.
Mount Madison is a good goal for an above treeline hike
if you have a good day. This mountain can be deceptive. The route up Valley Way to the hut is sheltered and easier than other ascents. The hike from the hut up Osgood Trail is fully exposed but is often protected from the winds until near the summit ridge. However, I have also been up there when winds were literally clearing my tracks within seconds and erasing any sign that I had been there. At any given time, there were only 5-6 prints behind me as they quickly filled in and visibility was low. On the "right" day, this can be one of the most dangerous mountains in the Whites. On a clear, nice day, it's a stunning hike that seems modest for its effort considering its elevation.