I agree the Grand Seiko line is VERY nice and the spring drive is amazing. Tested more stringent than COSC standards. That being said, I agree that it would probably earn more kudos to begin with a less expensive watch ($400-$1200 range). You would be amazed at the quality. Learn about the brands and the technology. That way you can talk up all the similarities and differencesthey they have to the big boys. Know the differences in the grades of the movements, the steel, the crystals, the lume, and the waterproofing. There are very nice COSCs that you can pick up for just over a grand. There's also great watches out there with top grade ETAs for $600 - $700.
This way you show that you know quality and value, and you truly know what the real difference is between a $500 and a $5000 watch (or $10K-$100K, oy vey). This will also help you make a more informed decision when you are ready to take the plunge on the real McCoy.
Fortunately, the big boys do hold their value on the secondary market. I've flipped many gen pieces without any trouble. You never know if a watch is for you until it's on your wrist. Here's some nice brands to look at...
MKII, Zenton, Hamilton, Seiko, Bali Ha', Bathys Hawaii, Boschet, Dievas, Halios, Helson, Korsbek, Kremke, Lüm-Tec, Magrette, Ocean7, Prometheus, etc...