Likewise, inscriptions can provide other interesting information. A few years ago, I sent an eBay listing of black dial Heuer Carrera to Ben as I knew he was interested in getting one. The watch happened to have a 1963 date engraved on the case back and I knew based on the fact it did not have a “T” above the SWISS on the hour registers and the other indications that it was an early Carrera. Ben ended up winning the Carrera, and it happens to have the earliest serial number known for the model. This fact, along with original 1963 print advertisements I found, helped to prove that the Carrera was introduced in 1963 and not 1964 as many thought. This story was even mentioned in Jack Heuer’s autobiography.

Keep an eye on the bracelet or strap, and buckle.

Each time I see a vintage watch on an expandable vintage bracelet, it seems to sell for far less than it should. Maybe it is because people have bad memories of them pinching their wrists and arm hair, but when I see those bracelets, I usually am happy because frequently the watches are unpolished and are original. That was the case with the aforementioned Heuer Carrera – it came on a junky bracelet that was not original. Let’s just say the watch looks and wears a lot better on a strap.

Likewise, you may just find a watch on the original strap with the original buckle, which should also tell you a lot about the originality of the piece. Given that original buckles can be worth hundreds of dollars depending on the brand and type, finding one can be a big plus.

You can’t wear a box and papers.

Although there is no question that a box and original papers is nice to have, you can’t wear them. In my opinion, it is better to buy an original and good watch then a piece in mediocre condition with the original box and papers. Not only can the papers be fake, as mentioned, but sellers will also go out and buy original boxes and papers separately to then match with the watch. This is not an ethical issue as long as it is disclosed, in my opinion, and can be a sort of arbitrage opportunity, but it is just something to keep in mind.

Are you going to spend four or five figures more on a watch because it has the box and papers that may not be authentic or original to the watch? It is just something to consider, and from a collecting point of view, can certainly be justified depending on the watch.

One other concerning thing I have generally noticed with watches that have original boxes and papers: they often are heavily, heavily polished because if the owner was obsessive enough to keep those, they were usually obsessive enough to have the watch serviced every three years, (and polishing the case or reluming the dial and hands was common practice during servicing.) You can also notice that the inside of the case backs of these watches have tons and tons of service marks. It is a double-edged sword – while it is nice to have a watch that has been kept up mechanically over decades, the associated polishing and other work on the case and dial can be a killer.

Exercise caution with certain brands on eBay.

There are certain brands which are better than others to buy on eBay. As a picky collector, I see very, very few vintage Rolexes that are worth buying. So many vintage Submariners, for instance, have heavily polished cases, replacement dials, or other problems. You also need to be careful with Rolex papers. There have been a few sellers who buy Rolexes with one account, create fake papers to go with the watch, and then sell them from another account. Just as very few vintage sport Rolexes are unpolished, very few come with the original box and papers.

In one example, flags were raised when people began seeing that every Rolex watch being offered by certain sellers came with original papers. Some sleuthing revealed other accounts (most likely associated with the sellers) buying the watches, along with vintage paper and vintage typewriters. When a friend happened to visit a particular seller’s home, he found the place was packed to the gills with vintage typewriters and old paper. Fancy that!

Factor in the cost of service.

Vintage mechanical watches require a service every so often (a few years) to work their best and avoid damaging the parts by not having proper lubrication. It is just good advice to consider that you will need to add the cost of servicing when you get the watch and you will want to have access to a good watchmaker to do the service. Behind every great watch collector is a great watchmaker.

As iron sharpens iron, watch collectors sharpen watch collectors.

No good watch collector is an island. It is worth learning from others and developing friendships is an enriching part of watch collecting. Maybe it starts on a forum or Instagram with a few messages being exchanged. Next thing you know, you are Facebook friends and then texting. And before you know it, your families are vacationing together. Well, maybe you won't get to third base that quickly, but developing friendships with others with similar interests can be extremely helpful. Those very friends can offer a realistic check before buying a watch and act as great resources for learning more about watches.

If you are interested in deals, focus on eBay auctions rather than those pieces listed as a Buy It Now.

I usually steer clear of Buy It Now listings when I am looking for watches. Why? They are generally overpriced. I prefer “barn finds” – those watches that may be coming from an estate. I actually prefer buying watches from someone with a whole bunch of random stuff listed for sale than a seller who just sells watches. Why? Originality.

Often, the seller with tons of different stuff listed is either cleaning out an estate or is an estate picker, who may generally have some ideas about watches, but may not be an expert. These estate-find pieces are often just the way I like them – with all original pieces. The nice feature eBay offers is that you can filter for just auctions or just Buy It Now listings if you like at the top of the search results.

That being said, there can be some Buy It Now deals.

Usually, the most incredible Buy It Now deals are snatched up shortly after listing – I am talking less than 60 seconds. I swear that there are probably over 100 people refreshing the Rolex Buy It Now searches every second hoping that some unknowing person will list a Rolex Milsub for $5,000, or something like that. (I know people that do it throughout the day with basically every brand from Heuer to Universal Geneve. And sometimes, you can get lucky.)

There is no question that there have been some unwitting people who have listed rare watches with a Buy It Now listing that is a fraction of what it should be. But generally, the longer a Buy It Now listing stays up, the lower the odds are that you are finding a good deal, unless you are going to bargain via the Best Offer function (if the seller offers that option).

Check if the watch has been relisted.

If it has been relisted, there probably is a good reason it did not sell. Perhaps it is a refinished dial, the movement is missing pieces or in bad shape, or it is simply overpriced. I am not saying that you shouldn’t bid, particularly if the seller has been reducing the price each time it is relisted, but you should exercise caution. If no one else is bidding, are you missing something?

Examine the seller’s feedback.

Does the seller have a lot of negative reviews and a rating far below 100%? If yes, that may be a person worth avoiding. Is it a seller with a "0" rating, or perhaps an account only recently opened, with a bunch of low-value transactions in a short period of time? Those are also causes for concern.

I remember reading about someone buying from a watch from a seller with a "115" rating, but then it turned out to be a scam and upon further review, the past transactions were all extremely low value transactions of odd things (such as feminine products) that had clearly been faked. Possibly, it may have been a bunch of accounts started by the same person in order to build feedback in order to do a higher-level scam sale of an expensive watch.

In any event, when I am examining a seller, I like to see a mix of items for sale (sort of along the lines of the seller being someone just listing things for sale from an estate) and a history of positive feedback going back many years (the seller doesn’t need to have tons of transactions over time, it can be sporadic feedback that may be realistic of an average eBay user).

Look at the bidding history.

Shill bidding is a problem, and it is important to know the signs of shill bidding. Are there tons of bids back and forth between two low- or no-feedback accounts? That is usually an attempt to drive up the price and should be a cause for concern about the seller and watch.

Avoid off-eBay deals.

It is worth nothing that just about any time someone lists a nice watch on eBay, they are hit with a flood of messages asking how much money they would want for the watch – if they would accept [insert lowball offer] and/or if they would remove the listing and do the transaction off-eBay (under the guise of saving eBay fees). This is a very dangerous game because usually the offers are far less than the watch should get if the auction ran its full course and because there really are a lot of scammers out there. If you do the transaction off eBay, you don’t have the protection that eBay offers.

Now, when I see a watch I want, I message the seller imploring that he or she does not accept any off-eBay deals because the price will likely be lower than if the auction ran its course.

eBay favors buyers.

Over the past few years, eBay has become much more buyer-friendly. This includes the fact that sellers can now only leave positive feedback for buyers and that eBay will work to refund purchases that do not arrive. It is important to review the return policies of a seller – it is, of course, preferable to have a seller that is willing to take the item back for a refund within a certain amount of time.

Honestly, I have had such good luck with eBay that I have recently only needed to request eBay’s help on one occasion: when some ultra-rare vintage watch tools never arrived from a South American country. I bought the item and then saw that the seller had shipped it and provided a tracking number. About a month passed when I realized the item had not arrived yet, so I went to the country’s postal service site and tracked the package. It had apparently been delivered, but within the country. I wrote the seller asking about the issue and he was initially responsive, then stopped responding to my messages and e-mails, so it became clear it was a scam. I believe the seller had intentionally shipped it to another address in the country in the hopes that I would not notice and time would run out before I could request a refund. Just something for you to keep in mind when buying items online (of any nature, for that matter.)