First of all, nothing wrong with Citizen and Seiko. The Citizen Campanola and Grand Seiko watches are to die for. Seiko Spring Drive can be just as accurate as a quartz, although it is a mechanical.
With that said, I consider myself a WIS and have 25 watches in my collection. It ranges from a few thousands to 6-figures watches.
Nothing wrong with Rolex, and it is by far the best bang for your buck. You can wear it till kingdom comes and it still ticks. Very touch watch, and mostly likely hold its value the best. However, most Rolex wearers are non-WIS and so they really don't know much about watches, hence their nose up-in-the-air attitude. Rolex is an entry level luxury watch, no more no less. They do heck of a marketing though.
For the money you throw at Rolex, there are many other brands that are even better. It depends on your life style. The best value watch I think is Maurice Lacroixe (they are also very under stated). Make sure you only purchase their Masterpiece line of watches. They have a broad line of product, from dress to sport, to GMT, to Flyback and Regulator. I have two ML myself and would recommend anyone to own one.
If pilot watch is what you are after, you cannot beat the IWC Spitfire Chrono, or the Mark XVI. You can have them on Croc strap or bracelet. They can be dressed up or down rather nicely.
For dive watch, I personally prefer a more none traditional route. Most people will go for the Omega Planet Ocean or Seamaster, I opt for the Ulyss Nardin Maxi Diver. They are a little bit more than the Omega, but one you don't see everyday. If cost is a consideration, a Stowa ProDiver is not a bad choice. It is a German brand, and that will get you away from the Citizen and Seiko crowd.
For the Chronograph fancy, again, you cannot beat the IWC Portuguese Chrono. I have the 3714 in white gold. Get compliment everywhere I go. The best is no one even recognize it is WG. They think it is stainless steel. No worry about having my arm being chopped off.
If you have a little more money to spend, don't over look other brands like Chronoswiss, Glashutte Original, and Blancpain. For lesser money but prefer something different, you can check out Ball Engineering, Nomos, Limes, and MeisterSinger.
For big bucks, you can never go wrong with the Lange, especially the Langematic or Lange 1. Or the AP Royal Oak. But I think you are not talking about spending a 6-figure.
Watches are notorious bad investment. I would recommend you buying a "slightly" used one and save more than 60% off MSRP. Check out the Sales Corner at Home Page - TimeZone
. You will forget about Breitling in a hurry. As a matter of fact, that's one watch you will never find in my collection. So is Heuer.