I started colecting good watches when I inherited a 1951 Rolex 18 k ref 6092 in 1990 , complete with box ,receipt of purchase in Hong Kong , papers , chronometer test certificate for watch and even the little sticker with price tag as seen in jewelry shops, with hardened leather band and Rolex buckel. ( Will post it next). I gave this to my elder son and had to buy another 6092 to give to my younger son. Started looking at the watch shops in Melbourne and Sydney and got hooked.
Having made friends and gained the confidence of a dealer in Armadale, Melbourne , I bought 2 more 6092s and a host of other Rolexes , from 1920s to 1980s and other well known brands. Sold many pieces that are too big for me to wear , including 1803 , pricisions and surplus ones like pillow shaped 1930 Rolexes and 2 Princes with 'observatory quality' movements. Kept those that I like until today My daughter in law wanted a new mid sized Rolex 3 weeks ago and we went to the Pavilion watch exhibition , where I met up with Scott.C and Takashi , with a Rolex 6567 Gold 14 k in my pocket , to take to my watch technician to get a new leather band instead of the gold bracelet. As my son preferred the newer 6567 with leather , I now have my Rolex 6092 back with an Oyster gold bracelet to wear and a spare 50 grams worth of 18 k gold bracelet with a Rolex logo(non original, but beautifully made), bought from a jeweler many years ago.
One should have a budget and decide what are the brands that one appreciate most. The pre-owned watch world is a jungle , even experts can be fooled. The most important thing is get recommendations from good friends and not from adverts. Word of mouth is important. I have learnt recently how to post a picture on MWF and get to identify the year of manufacture of my Omega Constellation with help from MWF. I have many books on Rolex and Patek , but not on Omegas. One is never too old to learn.