First step: Pick one of the known brands
Yes, sure, you can buy a Rolex tomorrow but don't expect to gain any value in the short-medium term. If you want to have something valuable, you need to go vintage. Double Red Subs, Comex, Paul Newman's Daytona, Big Crown's Subs, McQueen's Explorers... There is a lot to be learn. The internet is your friend. You don't have to set aside $32,000 for your first vintage watch, you could easy get a 5513 Submariner for as little as $5000 and end having a nice piece that will gain some value in the future. Other brands like Richard Mille already sold out the RM035 Rafael Nadal at more than $500,000 each. And even the Urwerk UR110, that's so hard to come by is already sold out everywhere. So when Audemars Piaget announced the limited edition Grand Prix (only 1750 pieces), we were on the waiting list and we didn't get one. They sold for $38,000. Another thing is to learn to be patient. While waiting for a Panerai Marina Militare Composite Case, limited edition for 2010, we were tempted by another watch. We took the bait and now we put our watch budget on jeopardy and we are hoping not to get the call from Panerai too soon... Depending on what you want to buy and what you love, you can collect Swatches, Timexes or just about anything that speaks to you. You just need to choose if you want to make money at the end of the journey or just to pass the time.
Limited editions are king
Every manufacturer is making some sort of limited edition/limited run these days. The less the number, the faster they will go. Panerai made a limited edition watch for collectors that sold out in 2 days. It's all about being at the right place at the right time. You will become a hawk, checking the forums for rumors and being ready at the international watch events (Baselworld and SIHH Trade shows) where all the goodies are usually announced. (and where all your money will go too!)
IWC Ceramic Top Gun with the Doppel Chonograph
Mechanical Complications: More is more!
Automatic movement, manual wind, power reserve indicator, double chronograph... even tourbillons! it's all about that little machine that is fitted inside your watch that would provide all sorts of information to its owner. There are even lunar phase watches and some that even tell you how often service is needed. The more complicated the watch, the more money is going to cost, and another thing to consider, is the provenance of the movements, or for better term, if the the company actually makes their own movement or commissions some other swiss atelier to make the movements for them. (or modify base movements at their own facility). Choose wisely, because you could end with a Ferrari and a Ford engine.
No trendy designs allowed
Big diamonds on the bezel? Skull and bones on the dial? Leopard strap? You can forget about those. (Unless you want them for your personal use and not as investments) You need to focus on classic, timeless designs. Manufacturers with history and heritage. Don't expect a return on a watch company that has been around for 3 years. New materials always catch the eye of the collector... Watch cases made of DLC coated steel, forged carbon fiber, ceramic or composite material are always a plus in the collector's community and people will pay a premium over the standard materials.
Where to buy and do research
For a first timer, I would recommend going to your brick and mortar authorized dealer. Not only they will take good care of you but there is the guarantee that the watch you are getting is original and it will include all the paperwork/certificates/boxes, etc. Also there is the piece of mind knowing that you can return the watch if you get buyer's remorse. Once you have been around the block, you can start venturing on enthusiast's sites and forums. Hodinkee, 10 Past Ten, TimeZone, The PuristS, Paneristi and some others. Go there, browse, register and ask questions. It's a friendly environment and users more likely will help you out. After you worked all the forums and sites, you may be ready to buy your first watch online from a private party. Ask for plenty of pictures, details about the watch, condition of the case, strap, glass and even for references. The advantage of a private deal is the discount you could get on a hard to get discontinued piece. For example, we were able to get an IWC Doppel Chronograph that the MSRP is $11,900 for $7,000 from a private party. Watches are luxuries and collectors buy them with disposable income, so when the time to sell comes by, you may get a good deal. That's your opportunity.
What to expect to pay
If you go to an authorized dealer, you can expect to receive at least 25% discount on the MSRP, with some brands (Like Omega or Tudor) offering up to a whooping 40-55% discount. So you can shop around 'til you get a deal, but be aware that some brands don't offer any discount at all, and you can forget about getting any discounts on limited editions.
Keep all the boxes and packaging materials
Watch collectors are very picky, anal persons. All the little details matter at this point. The difference between a watch that doesn't have any box or papers is around 50% of one that has all the stuff in place. So keep EVERYTHING! (You will thank us later)
At the end, have fun collecting watches! They are an investment that you can enjoy and when you decide that you don't want them anymore, or your collection style shifted directions, then you can sell them for a profit (if you did your homework at the beginning), so you can buy the next one or cash in and take that caribbean vacation you always wanted.