Agree with much of what you say. Have you tried Skipjack? It is normally used for racing and besides, most people just blow by the entrance to the trail at Mach One and because of that, the trail is, and maintains itself. extremely well groomed.
I understand the next expansion is going to be in the Cupp/Shays area to fully utilize the under-used detachable quad there, and they will end up making several new trails on that side. I hope they are all black because that will keep the beginners from that side and prevent the safety mess that occurs on the Eastern side of Snowshoe.
I will say it again -- on Holiday Weekends, I would NOT recommend Snowshoe. The ski trail layout versus the crowd size is, IMHO, unsafe during those weekends, and if they end up making blue trails on the Western Territory, they will end up f-----g up that side too. On holiday weekends, I put my condo for rental and save myself the frustration of having snowplowers on a black run becoming a life insurance risk. I applaud their making all the green trails by the Powder Ridge lift, Yew Pines and the other Yew family. Hopefully that will keep the different experience levels satisfied and avoid hazardous experiences. This year, I have used that side for my warm-up runs and then gone to the Widowmaker, Knot Bumper and Skipjack side, then over to the Western part.
I respectfully disagree with you on the mountain layout. The upside-down setup is what got me to buy there. I like to drive up, park my car, and forget about burning fossil fuels until I have to return home. The setup there allows virtually everything to be within walking distance or a shuttle bus, and once the new Village is fully built, it will look like Tremblant, Stratton or Whistler. Besides, the million-dollar views can't be had from a base-side lodge.
Once the "Village" is complete, I think you will love Snowshoe. It will be more skier friendly, more upscale, more geared towards a four-season experience, and catering to a greater crowd, as you will be able to take your non-skiing friends and they will be able to enjoy alternative sports, cultural amenities, and of course, shopping. I guess the models are Tremblant, Stratton or Whistler, and if you've been to those, they can certainly be amenable.
Agree with an upside down resort you won't have the crowds gathering at the same spot. But with some good human factors engineering, this can actually be a plus because it would avoid the crowding that one sees in "normal" ski areas. Besides, it would be nice to have the ski areas more-or-less divided into experience level areas so one can ski at one's level of experience without becoming either a safety risk or an obstruction.
In this factor, I REALLY like Wintergreen. The skiing conditions are not as good as the Shoe, but the mountain is definitely more organized and in order to descend to the lift that serves the black runs, a skier has to pass through a "gauntlet" with ski patrol watching. If he/she is not able to ski at the appropriate level, he/she is ushered to the trails leading to the blues and the greens.
Also in the mid 2000's they are starting work on the third mountain village (when at the base of Snowshoe area, the mountain across the reservoir) that will be home to a new village and a slew of new trails.
That is the plan -- also the entire village is going to be redone (As many people mentioned) and as far as Timberline goes -- I heard rumors they sold Snowcats last year to pay a tax bill. Who knows.