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i don't know your annual income, asset base, marital status or amount of or plans for children. I think your best bet is to establish an annual watch fund that correlates to your income. Obviously, housing, college and retirement savings come before watches.
I would not engrave anything on a watch that I might sell in the future. I doubt that I would buy a used watch with a personal engraving. But some people might like it.
Don't want to be a curmudgeon, but I am a conservative spender and investor. One cure for the watch jones is to buy something inexpensive and fun like a Hamilton, Tissot, Frederique Constant, etc. , then go AP or Rolex after a great income year or bonus.
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