First purchase 16233 help please

[cluelessfiance]

Hi everyone,

I'm looking for a preowned Rolex for my fiance as a wedding gift (something classic like a two toned DJ 16233). Preowned because I figured like a brand new car, you lose some value as soon as you walk out of the store with it. It would be his first luxury watch and I figured our wedding is a better time than any but I need some general advice since I'm clueless!

- How important is it that it come with original box and papers if the watch comes from a reputable seller? I feel like I see an upcharge with these watches

- Can anyone explain the variability in price? I know some of it has to do with how its running, original finish, if its all original parts and the year but what matters the most to you all?

I've seen a few watches anywhere from early 2000s with "light to moderate wear," all original parts that have been polished that are in the 5K range. I've also seen the same watch, maybe 2005-2009 with factory stickers still on it that are anywhere from 8-9K. I understand it's pretty much brand new and would obviously cost more but does double the amount seem reasonable?? Or is it that much more because its newer? I think the newest version would cost around 11K but I could be wrong.

Thanks in advance for reading this lengthy post, I figured you all would be the best people to ask.