Ha, you're in Denver?! Awesome! This might be the very first time that I've run across a Denver resident on a GMAT forum by complete accident. Good stuff.
So I guess the really important question is, why the heck are you wasting time on the GMAT when you could be skiing or snowboarding instead? Can't the GMAT wait until spring?
The trouble with the GMAT is that there really isn't an easy, one-size-fits-all answer for everybody. Most of the people you'll meet on this forum will ultimately spend quite a few months studying like crazy for this exam. Some people nail it in a few weeks. Some lucky people study for a few hours and manage to get away with it. Considering that the GMAT has already humbled you a couple of times, I think you should be prepared for a few months of pain... and there's no shame in that at all.
Hopefully a few others will weigh in on this, but I think the biggest advantage of a class (or a tutor) is that it will give you some structure, and you'll have to complete a certain amount of work between classes... and that can be awfully appealing, since it isn't always easy to come up with a self-study program on your own. Then again, it's rare that a class works perfectly for any given individual--depending on your exact strengths and weaknesses, you'll find that some classes are too fast or too slow or not thorough enough or don't address the topics in a way that matches your learning style. There are a ton of solid classes out there, but they don't work for everybody.
If you decide to do self-study, you'll definitely need a plan of some sort, and there are plenty of resources on GMAT Club that can get you started. Many people love the
MGMAT books, so you might want to consider those if you don't sign up for a class. No matter what you choose, you should be prepared for a long slog through the study process, and if it ends up being easier than you expected, then thank the GMAT gods... but don't underestimate the task in front of you if you're trying to improve by 100+ points. And don't fall too madly in love with study materials from non-official sources; if possible, the vast majority of your practice should be from official sources.
Good luck with everything! See you on the slopes?