Good points, peakbagger.
Unfortunately, most "new" hikers never look at the guidebook. Guidebooks in most areas are a wealth of useful and potentially life saving information. We have the same issue in the Adirondacks. Most new hikers read an article in a magazine, ask a few questions on facebook, and away they go. This results not only in lost person incidents and rescues, but also damage to the resource. As with many things, education is the biggest challenge.
Interesting that you note specific places where it's common or people to get lost. Clearly, this is common knowledge, so the State and its agencies should know this as well. Given the current legal environment, I think it's only a matter of time before someone is charged for a rescue in one of those locations, and their attorney makes the argument that the common knowledge that these places have this problem "creates a duty" on the part of the state to improve signage there. And that argument actually makes financial sense for the state. I don't advocate "big neon signs everywhere" (the straw man). But if there are a few places where we know there is a problem, an investment in a few big, "obvious even in winter" signs would easily be paid for if it prevented even one SAR incident.
The places he named are more like places to drift in and where you can't see where the trail leaves the open summits and re-enters the woods. It's not hard finding the trail down Jackson back down the Webster-Jackson trail but finding the Webster Cliff trail heading towards Pierce & Mizpah. (I've had to wander a bit finding it myself) The USFS did have a suit back in the 1990's when a skier (I believe) died when she fell behind the snow pack in Tucks when it left a gap late in the snow season as it melted away from the headwall. Think USFS won but it may still be ongoing or was settled for an undisclosed amount.
Not sure about if the New England Trail Conditions site has a Q&A place or if Rocks on Top is still up. I know currently NETC is getting more trail condition reports than VFTT is now. If you are reading just NETC, if you see some vets doing these trips, you may think it's easy to do. Getting trail condition reports and not knowing much about who posted them, means you may be following an idiot or someone who's so good, that they skip by hazards that new winter hikes don't understand. You and I can get by with 50-75 feet of visibility. It helps to not only see a Trail report but know if that person is a trail animal capable of super fast hikes & with years of winter experience up difficult terrain or an out of shape newbie who thinks five miles is a death march. (Think of the different answers you get on ADK HPF depending on the persons risk tolerance)
Could GPS be hurting? If you don't have all your waypoints in, you may know where you are but not know where to go, They may be overconfident in going ahead even with Waypoints thinking they can't get lost but underestimate the time needed to cross an open ridge in very poor conditions.
There are some summits in both places (NH & NY) where you can learn about above treeline conditions without being in wide open places like Marcy or Washington. (Have they agreed that these two missed the turn on Lafayette and ended up on Garfield Ridge and had not attempted Mt. Garfield as one of the two initial press releases said.
In NH, Liberty, Pierce (can drift in very high but some basic knowledge of where the C-Path and Webster Cliff are help) Garfield, Jackson (up and back on Webster Cliff or up C-Path, Mizpah Cut-off and to Jackson to avoid the drift problem mentioned by Peakbagger, at least the first time) and South Kinsman (after going over north) provide some open summits with small open areas and are not hard to get too.
The High Peaks don't have as many but Phelps comes to mind and Cascade (Cascade's open summit area at the larger side of a learning location) and then peaks like Noonmark, Hurricane and Hopkins but I'd guess that not many people are doing the open lower peaks. Saddleback might be on that list for the summit area but it's a pretty long haul and wouldn't want new hikers between Saddleback and Basin.