Just out of curiosity, are you rich because you have a little boat and can afford 2 (two) Rolexes, or do you have a little boat because you are not rich after buying 2 (two) Rolexes that's all you could afford?
Super fair question. I have a little boat because (a) I'm on a lake (b) I had never sailed before (c) I single hand all the time.
I actually started out after my ASA classes looking for a Catalina 30 and while on a cruise with a seller I realized this was crazy considering I wasn't sure this was 100% for me and I was only one guy.....so I decided to start with a C22 and work my way up....
Actually the fallacy that Rolex do not keep time is crazy, they are automatic watches after all and will never keep time like a quartz watch or a phone. My group keep time with +/- 10 seconds every 10-14 days which is more than adequate. I have them pressure tested once a year and regulated to the cost of $50.
They do need to be serviced every 7-10 years at the cost of $600, but I have never had mine service as the are between 7-10 years old and still keeping great time.
As another poster noted, all my watches are worth more today than what I paid for them

that never hurts either...