Relatively short lift lines on off peak days
As a native Vermonter I am used to the smaller resorts that the Mid Atlantic has to offer. Usually the short comings of the terrain are made up for by having a great staff and plenty of amenities. This was not the case at Timberline. To begin with the rental shop is poorly organized and many of the employees were just plain rude. It took almost an hour to get our equipment thanks to understaffing despite the fact that there were relatively few people in line the first day we were there, the second day took even longer. When we finally did get our skis not only were they out dated, they had not been waxed in ages and we had to pick poles that were mismatched and in many cases badly bent.
The resort claims to have three lifts, however it counts its bunny slope lift as one of those three so in reality there are only two (only one of which services the top of the mountain). On New Years Eve the lines were manageable, mostly due to poor weather, but on New Years Day the lines for the lift to the top were averaging a twenty minute wait. Add that to the slow lift speed and you can anticipate around 40 minutes bottom to top for about a 5 - 10 minute ride down the slopes.
The lodge itself is decent but the service is very poor and the food is nothing special if you plan on eating lunch. It took around 45 minutes to get a sad looking sandwich and a beer only to have the waitress screw up the bill and in the end add more than she had originally. I will say that the beer is cheap though so if you have someone with you who wants to do the lodge thing it might be a consideration.
Ultimately I can not recommend Timberline to anyone who enjoys a ski vacation, you will be disappointed. On the other hand WISP is around 35 miles away and is a much better resort in every aspect.