Whether you're shopping for furniture, appliances, or a sweet new ride, Craigslist is likely on your radar, and it can be a real boon to savvy shoppers. On the flipside, it can be a total boondoggle. Sometimes the deal just presents itself to you; a quick search yields exactly what you want, well-priced and nearby, but that's kind of the Craigslist unicorn. More often, you need to search diligently, negotiate, and brush up on your Craigslist algebra. Here's how:
Know what you want. If you have a specific need then have your parameters clearly defined. One day I decided that a Scandinavian secretary desk would solve all of our entryway problems, but it couldn't be wider than the narrow strip of wall separating my tiny foyer and living room. It took 10 months to find one that fit the bill in terms of size, price, function, and aesthetics.
Figure out your search terms. Searching Craigslist is a skill unto itself. Depending on what you want, your terms may be general or extremely specific. Searching for a particular brand or designer is pretty straightforward (although some sellers will use certain designer's names as tags for items of a similar era or style), but once you get into the realm of unbranded vintage it's an entirely different process. If you have time to kill then broad search terms like "vintage" or "mid-century" could yield great finds, but count on sifting through ads where those terms are synonyms for old and ugly. If you're looking to coordinate with other items in your home then you may want to search by pattern, fabric, or wood. Try common misspellings.
Oftentimes you know what you want but aren't sure what to call it. Stretch your imagination. I needed more chairs for outdoor dining but didn't know what ours were called (Emu Rio), so I would search "white metal chairs," "white patio chairs," "white deck chairs," "white grid chairs," and countless permutations. Eventually I turned up a great deal on a set of four.
Know market value and your budget. I'm in the market for a grill, so before I even ventured onto Craigslist I looked at what they cost new. Between Memorial Day and Father's Day, the market is saturated with secondhand grills from sellers who have upgraded, so a quick survey of Craigslist makes it easy to discern typical prices, inflated ones, and screaming deals (like the one I saw last night that sold within three hours of posting). Having a solid sense of my price range and what I want can save me from wasting time on posts that are way off-base.
Figure out your search schedule, parameters, and tools. I tend to obsess about things, so instead of setting up a feed or compulsively searching on my phone all day, I'm a first thing in the morning/late in the evening searcher. If it's something worth a longer drive, I might search nearby cities or use an aggregator (I like adhunt'r and will limit my search by region). If it's not worth a longer trip then I'll winnow down my search by location.
It isn't a deal if you spend way more on the back end of the transaction. Those chairs with great bones may be dirt cheap, but ancillary costs can add up quickly. Figure it all out in advance or you'll find yourself reposting the item or putting it out on the curb. Will it fit in your car? Measure and measure again, or face renting a cargo van or truck. Do you plan on getting something reupholstered or refinished? That can get expensive, so it's worth getting a quick estimate before purchasing the item in question.
Write a good inquiry. Ask the right questions for the object in question. For kids' gear I always ask if the seller is the first owner, along with the year of manufacture (a quick search can rule out safety recalls). If I'm emailing someone about a grill I'll ask if they are including the cover and propane tank. For upholstered items I will always ask about smoking and pets, as both are non-starters for me. I might ask for more photographs or specifics on condition. I'll also provide my email address and cell number, so that the seller can contact me by email, phone, or text, whichever is most convenient for them.
Let the seller know that you are motivated, nobody wants to waste time with a tire kicker. Complete sentences, please and thank you, and an indication of good faith seem to go a long way; something along the lines of "if this is a good fit for my needs I can pick up at your earliest convenience, cash in hand." If you think their asking price is fair then there's no need to negotiate. Otherwise, start with an initial offer below your target price to leave room for negotiations.
Inspect before handing over the cash. Look everything over, make sure that the item is as described and in the stated condition. If not, be prepared to renegotiate or walk.
Find your Craigslist zen. There will be the perfect fit that sells out from underneath you, the unresponsive seller, the intransigent price inflator, the one who only wants to communicate by carrier pigeon. If it isn't worth it to you, the seller sounds sketchy, or your spidey sense is going off then be prepared to walk. It isn't yours until it's yours, so don't waste time grieving the one that got away.