Big, Good facilities, good snow, great hero groomed cruisers, wide runs, fast lifts, lodging
Not many classic narrow trails, HORRID layout, rude people
As stated in the title, you either love or hate Okemo, depending on what you're looking for.
You will love it if:
You are an intermediate and like wide open, smooth cruisers, want good, reliable conditions, even in a bad eastern snow year, like lots of things to do after skiing, want fast lifts, like sick terrain parks, like fancy lodging and good food, and are looking for that "quaint Vermont flavor" that people flock to Vermont for.
You will hate it if:
You are an advanced skier looking to scare yourself, like narrow, twisty New England trails, hate crowds (on main lifts), don't like a very resorty place, or you are low on cash (expen$ive), or you have a problem with crowds from New York/Jersey/Massachusetts (yes, I am from Mass. Guilty as charged).
If you, like me, apply more or less to the "hate it" category, you might as well stop reading. If it sounds appealing so far, I'll try to give a few pointers.
First and foremost, ski it on a weekday! You'll have the place to yourself. If you are driving from pretty far, stay for a few nights; the lodging and off-hill activities make up (almost) for the less-than-challenging skiing.
Some pointers on the skiing:
Carry a trail map; the layout isn't great and the place is big. It's pretty easy to get lost. Try not to head to the main base unless you are a beginner. You have to ride up a beginner lift to get to the other lifts from there (really dumb layout).
Avoid the Northstar express quad during peak times at all costs. This can become the most crowded lift. Like any large ski resort, there are always places to hide from the crowds. For starters, any of the slower chairs (Green Ridge/Black ridge triples) are never crowded and get you to the same terrain as the Nstar express quad. If you want to avoid crowds without sacrificing chair speed, head over to South Face. Some of the better terrain is here and there are never any bad lines here. It's a bit of a haul to get there but it's worth it. Also, the Solitude area of the mountain is true to its name, and has a high speed lift, and there's even a good restaurant there, as well as lots of nice condos. Jackson Gore has the most challenging (relative) terrain on the mountain, but the high speed quad there can get crowded, and getting there from the main mtn is pretty annoying. Get out early for great snow. I'll admit that grooming is one of Okemo's strong points. This is especially fun/easy if you're one of the lucky folks staying in the mountainside condos!
I am not very familiar with this, but I'l try. There are lots of restaurants and condos, second homes, and hotels around the resort. Jackson Gore is the place to be if you like off-hill activities, like ice skating, fire pits, restaurants, fireworks, and new this year, a roller coaster that goes down the hill.
I hope this has been helpful. My problem with the place is the lackluster expert terrain, but I can see it being a great resort for others. Enjoy