If money is no object, I would get a box of the following:
A box of Padron 1926. I haven't tried many of the sizes, but I'm sure others can chime in on which sizes are best. The No.35 is a great, short smoke.
A box of Ashton VSG. The Enchantment is really good, but they really don't come in a bad size.
A box of Tatuaje Tainos or Cojonus. Great smoke if you have a couple of hours. Also, the Noellas are great for a shorter smoke.
Arturo Fuente Sungrown Cuban Belicosos. These are a great sungrown smoke. The King B's are also really good. They have a Rosado wrapper and are typically harder to find.
CAO Cameroon are some of the best cigars that CAO puts out and are typically easy to find.
As for harder to find, Anejo, Opus, and Hemingway Maduros are all great cigars.
There's my thousand bucks, give or take....