This is purely my point of view and i can be biased as i own the watch.
I believe rolex is still the watch that will retain its value pretty well. AP, VC and PP should retain its value pretty well with their reputation as the top 3 brands in horology. The classic models for these 3 brands are more in demand as their design are timeless in my point of view. End of the day, i don't think that retaining value should be a factor in your consideration, but take it more like a bonus. By trying to quantify the value, its like placing a value on a piece of artwork which is very subjective.
As fopr whether to buy it pre-owned or new, its really what you want end of the day as both has its own pros and cons...
New watch
Pros: New and never worn, save on servicing, worry-free...
Cons: More expensive (only concern)
Pre-owned
Pros: Cheaper (only pro i guess)
Cons: know nothing about the condition of the watch, servicing cost as pre-owned piece most of the time had not been serviced for some time,
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