I’ve said time and time again that the vast majority of my travel is subsidized by points and miles. Unfortunately, I can sometimes get caught up in only spending points/miles (and not cash); this can lead to missing some pretty great deals. I’ve tried to make a concentrated effort to be better about these things. I still firmly believe that a good deal is not the reason to buy something (one thing the love-him-or-hate-him Dave Ramsey and I have in common), rather it can be the impetus to buy something that you were already planning to.

I’m not sure I would call myself a skier, but I do enjoy going. My friend Josh and I would take annual trips to Snowshoe Mountain while we were in high school. From western Kentucky, that’s quite a drive. Fortunately, from DC, it’s much closer.

That’s why when Snowshoe Mountain introduced its Ridiculous Pass towards the end of last season, I didn’t even hesitate, I purchased one immediately. $200 got you not only the remainder of the 2012/2013 season, but also the entirety of the 2013/2014 season. When lift tickets run close to $80 per day, three days at the best ski slopes in the southeast more than pays for it.

In hindsight, I may should have been a little more skeptical. Not because the deal was bad, but because skiing is an expensive hobby and a lift ticket is only one piece of that puzzle. $200 assured my ticket back to the top of the mountain, but in order to use it, I’d have to find a way to the bottom. Most of the time this involves purchasing or renting ski equipment. My parents had given me equipment one Christmas in high school, but at this point, I probably needed to get that checked out.

My friend, John, recommended the Baltimore Ski Warehouse. They were able to check out the equipment, recommend that I should purchase some new skis (big surprise, I know) and confirm that the rest of my equipment was in good condition. Most ski stores can sell you previously used skis, boots and poles for around $200, which I’m assured are perfectly fine.

I tend to like to know a lot about something I’m getting, but sometimes you have to pay the stupid tax.[1. Essentially, you just can’t know everything about everything and if you want to do something you don’t know a lot about, you sometimes have to pay someone more knowledgable to help you with it.] Did I overpay for my skis? Probably. But if I wanted my own pair, I was forced to use the knowledge of someone who can make a good recommendation. As much as I hate it, sometimes that’s worth the money.

So with a season pass and new skis in hand, the only thing left to get was a place to stay. Unfortunately, this can be the most difficult part of the process. Especially at Snowshoe. The slopes are in such a remote area that unless you’re willing to pay to stay at the resort, you’re going to have at least an hour drive every morning and evening you’re there. This isn’t quite a “stupid tax”, but it’s in the same vein. Often you have to be willing to pay to make your experience more enjoyable.

As much as I know how to wring the best deals out of hotel chains, sometimes the best and only thing to do is to type “Snowshoe lodging rentals” into Google and be done with it. This led us to a private owner on Vacation Rentals By Owner. Since it’s still early in the season, the rates were only $140 per night for a condo that you could ski in/out of.

The trip itself was great. The crowds were small, but not all of the trails were open. Julie and I spent Saturday getting back in the hang of strapping two boards to our feet and pointing them down a mile-high hill. We could then spend Sunday trying to actually get better. There was no reason to push ourselves too hard; we’ll be back, that’s why we bought the season passes.

The amount of money you’re willing to spend will definitely vary, but if it’s in the ballpark of being affordable for you, I can’t recommend getting a ski in/out condo enough. For $140 per night, we could pretty easily go inside and warm up, or rest in a private space that had a place to cook and store food. That may not sound like you get a lot for paying significantly more for a place to stay (and if you’re going in January or February, the cheapest you’ll probably find is $300 per night), but trust me, it’s worth it. I never realized this, but a lot of my annoyances with skiing were more closely related to those ancillary things rather than skiing itself.

So was it worth it? I think so. But a good deal on a season pass turned into new skis and a fairly expensive place to stay. That’s one thing you’ve got to a remember when you find a good deal: look for the incidental costs. There’s always incidental costs.