I took my family to Timberline over this last Christmas break. I have pleny of "pros" with only a couple of cons.
Laid back, "mom and pop", "old school" feeling ski area. Not much (as in Zero) "flash" or "attitude" (I prefer it that way). No "village", upscale shops, restaurants, cobblestone streets, etc. - and much of that probably translates into the very reasonable prices. This makes it a very family friendly area since a trip there won't break the bank. Some people use the word "rustic" to describe some of the somewhat outdated facilities in a polite way...but I actually like "rustic".
A true 1,000 ft. vertical. The vertical compares very favorably to practically every other area in the region. Snowshoe touts their "1,500 ft vertical" number - but that only applies to 2 black runs - 95% of Snowshoe only offers 700-800 ft. vertical. Most all of the runs at Timberline, however, use the entire 1,000 ft - provided they are open (see snowmaking comment later). I like the fact that even my kids can ski top to bottom - the "Salamander" run is 2 miles long and the kids love it. Feels like skiing a "mountain" rather then a hill.
Really only one "con". They still need more snowmaking capability. If you want to ski all of the runs from the top of the mountain (and/or most black runs), you need to wait until late in the season. When we went, there were only 3 runs open from the top. Since the kids don't want to ski a black, that only left 2 (Salamander and Twister). It can get a little boring doing those same 2 runs over and over. Even today (Jan. 6) there are still a lot of runs not open. I don't think it is a result of lack of cold weather, I think they just need more capability. It looks like much of their snowmaking is composed of portable guns that they roll from one run to the other - unable to make snow on "every run, every night". I may be asking for too much, or course, since snowmaking costs money and I am also fond of their reasonable prices.
My other two "cons" are really just a wish list to make a good thing better.
- I'd love to see one of the 2 old triple lifts replaced with a high-speed quad. That would be icing on the cake for what is already a very plesant ski area.
- There are alot of slopeside homes on the bottom 1/3 of the mountain. That is fine, but I wish they would set those houses back in the trees a bit rather than lined up right on the edges of the trail. Skiing down Winterset feels a bit more like skiing through a sub-division rather than skiing down a mountain.
Overview: Very nice (if a bit 'rustic"), family friendly, reasonably priced ski area with nice long runs. I just wish they were able to open more runs sooner in the season.