Here are some general guidelines to keep your watch in top shape. These are not all of them but they are the most important ones.
Travel light. Resist the urge to travel with your most expensive and cherished watches.
Tourists are a great target for thieves. Hotels are always a risk for your most precious belongings. Remember... three (watches) is a crowd.
When you travel keep the watches as close to you as possible.
Keep them in your pockets at all times bags are generally the target. Suitcases are a big risk!
Careful with purchasing NOS (new old stock), they might need a service even if they never left the store.
Watches that are displayed can be either subjected to heat (if displayed under halogen light or directly under the Sun) and longer periods of inactivity (in the safe). This renders the lubrication of the movement inexistent or ineffective. Even if the discount is very appealing, calculate the cost of having it properly serviced. Sometimes it pays of to buy a "fresh" watch or just walk away.
Choose the place where you hide your watches at home carefully.
Don't hide them in your bedroom, kitchen or bathroom. This is where most people hide their stuff and where all thieves look first. Having two safes, one in your bed room as bait and one with the real stuff hidden in your living-room for example.
Resist the urge, don't try to play Doctor with your watch.
If you are not very skilled try to avoid changing straps, removing links or cleaning the watch. Sometimes if not done properly can be very harmful. Your local Jeweler will most likely not charge you for minor things such as that.
When adjusting a bracelet bare in mind that your wrist will have a tendency to swell with heat.
This is true for most people although some swell more than others. Especially in the summer there can be a full size increase making your watch too tight for your wrist.
Enjoy your watch before you spare your leather bracelet. The leather is not meant to last for ever.
In most cases leather bracelets are a fraction of the total cost of the watch, don't worry about them to much. If you must, jump in the sea with it or shower, it's leather at it will deteriorate or even start to smell over time. You are most likely going to change the strap before it is damaged by water. A strap change every year will make the watch look great again and you will have enjoyed it far more.
Watch out on eBay! Unless it is impossible to find anywhere else try to go to your official local dealer.
It has become a classic for people to get coned over the net and the tendency is growing. Special limited editions are the cons favorites. Most dealers there are honest, just remember to research the seller first. If you are not familiar with this find someone who is. Most of the times the deals are the same as on the street anyway.
Do not expect watches to be a good investment.
Even though they do better than cars very few people can actually make a living from buying selling in the secondhand/grey market. If you buy it, make sure you like it first.
Use the Internet.
It has never become easier for a buyer to inquire and ask other about product satisfaction than today. Ask people on Forums about their views and knowledge, they are a great source and a good way to acquire knowledge. Most people there are very helpful and no mater your initial knowledge they will be able to answer all your questions and shed light on your most obscure doubts.