The three most important and most expensive purchases you will make are your kayak, your tent, and your sleeping bag. If you are on a budget, you can skimp on everything else — but not on one these three.
Quality & Cost
When buying gear, you get what you pay for — up to a point. Most of the high-end expensive gear isn't better than the mid-priced stuff. It doesn't last longer, it doesn't perform better, et cetera, so don't waste your money.
There is also a tendency for companies to sell marked-up versions of basic items. That expensive "bear bag line" or "clothesline" at the outfitters is just rope. That's all it is, so might as
well pick some up at the hardware store instead.
Regular Sales: Labor Day & Christmas
If you really want to save money, then wait to buy things like your clothes, tent, sleeping bag, paddles, stove, et cetera until the magic window of Black Friday to New Years Day. There are so many deals, sales, discounts, coupons, manufacturer's rebates, and offers of free shipping during that time that you can save hundreds and hundreds of dollars. My strategy is to do my research throughout the year -- read gear reviews, compare options and features, and make purchasing decisions early, before Christmas. Then, when the sales begin, I keep an eye out for everything on my list.
If you do this, don't worry about not getting the latest and greatest. Yes, the next year's models are about to be released the following spring, but it doesn't matter. I sense a great deal of anxiety from people about not having the latest models with the newest features, but frankly once you have been doing outdoor sports for a couple of years like I have, you realize how little things change. Those latest and greatest features are always superficial and not worth the extra money. Substantial, transformative changes in technology and materials only happen every few decades.
One caveat: In my experience, kayak retailers rarely have Christmas sales or deals. Instead their sales are determined by the paddling season -- big sales of unsold stock and store display / demo
boats usually happen in the fall or early winter, after the summer season. If you are looking for a deal on a kayak, wait until then or check out Craig's List, which I talk about here.
Where to Shop
I have just one piece of advice as to where to shop for gear: always shop at kayak outfitters, whether in person or online, not boater supply stores. The gear sold at boater supply stores like West Marine and Boater's World is not suited to kayaking and long-distance touring. The gear is typically heavy, bulky, low-quality, and way overpriced.