I've enjoyed reading your posts over the past few months as you agonize over the decision of getting a Submariner versus buying lower-cost but still high-quality alternatives like a Doxa or an MM300. A couple of observations:
1. Being a disciple of Dave Ramsey and buying a luxury watch are simply incompatible. Dave would tell you to buy a Casio MDV106 and put the rest of the money into paying down your mortgage.
2. Customers of your funeral home will indeed notice your Rolex (its about the only brand non-watch enthusiast recognize as being "the best" and "very expensive") and will probably resent you for having what they believe to be such an ostentatious piece of jewelry on your wrist, which they figure will be at their expense in the prices you charge for services. It's the reason that in the 60s and 70s that doctors drove Buicks rather than more flashy Cadillacs or European makes -- they didn't want to flaunt their wealth.
3. No watch will satisfy you other than the Submariner. I can tell it by your posts and know that settling for lesser watches is always going to be suboptimal and won't end the yearning. If the Tudor didn't do it, a MM300 or 1200T certainly won't.
4. Believe it or not, an obsession with being debt-free and retiring early may not be the road to true happiness. My father was a child of the Great Depression and resolved to never be poor again in his life. He scrimped and saved his whole life working as a teacher with a very average income, but by the time he retired in the 1980s he was a millionaire. What did he do with all of his money after that? Nothing. He bought an inexpensive retirement home in Sun City, had one modest car, and within two years was diagnosed with cancer and died shortly after. No grand vacations, no luxury goods, no fine dining, no fancy entertainment -- he pretty much kept on living the same miserly lifestyle because that was all he knew before. I'm very sorry that he never got to enjoy his money but I think that what truly gave him happiness was just looking at his bank statements every month and seeing how much they had grown. The point is, there is a balance that should be maintained and that a maniacal drive to accumulate as much wealth as possible may not be the nirvana one thinks it is. It may give you solace to know that you have no debt whatsoever, but it does come at an interpersonal cost. As my father's child, I painfully learned that lesson when simple things like clothing were always purchased used, almost nightly screaming matches engaged over food not eaten ("there are people starving in India!" He would roar), and having to drive the family car without insurance because my father was too cheap to pay for it. He told us never to get in an accident and if we did, he told us to simply tell the police we didn't have any insurance and we'd be off the hook for any damages. I drove to high school in absolute fear that it would happen to me, but fortunately it never did. Don't get me wrong -- I loved my father and he was a good man -- but this obsession with accumulating (but never spending) money was a burden me and my brothers shared growing up.
My advice? Just get the Sub. Buy an inexpensive quartz watch to wear when you meet with customers. Wear the Sub when you're off-duty. Learn for yourself whether owning a Rolex is all you had dreamed of. I sincerely hope it does work out for you.
All opinions above respectfully submitted, of course.