New vs used Datejust

[samwellg]

First purchase coming up. I am torn between going with a used datejust between the 80s-90s or going new 2014.

First: the used Rolex I went to see was OK, the dial was very sleek and clean, very much something I am going for. However, the band wasnt something I could settle on. I really want the super jubilee, which I believe didnt get introduced until 2005-6. Price out the door - $3300

Second: Brand new rolex, it has the super jubilee band I want, but the dial is nothing like the old style. It seems a little busy, but it may be something I have to get used to. Price out the door -$7950

Third: This watch is best of both worlds, but the price makes it tough to really decide on. It has the super jubilee and the dial is sleek and clean; not too busy. Price out the door - ~$5000

Heres whats going on. I can go vintage and be satisfied, but with the hollow links, there will be some separation. Obviously too not knowing exactly how this watch has been serviced which does concern me considering I will be spending a few thousand. I want to go new so I have the piece of mind and lately I have been leaning that way completely. But now there is this watch in the middle, but still an older watch.

Pretty much: Is it worth going new and feeling great and just having to get used to the dial. Or spend half the money and not have that experience of a brand new watch. I understand Rolex watches hold value and are amazing pieces new or vintage, but itll be my first watch and a lot of money spent either way (on a watch at least).

Any advice?? Money isnt the issue, its spending wisely.