To me, get the classic Jumbo chanel in SHW... you will never regret it as the design will stand the test of time...
I personally think that vertical quilted bags are a little "dateable" and you will end up STILL hankering for the classic quilted.... and eventually getting one in SHW that you always wanted... etc... believe me that this is the start of many many many bags to come... ha ha!
Plus, if you purchase it new, you get the Chanel boutique experience, the magnetic box, the camellias and well... bag with SHW!
Be patient... you can do some homework and check out the current going prices for classic flaps around e bay or resellers... perhaps you might even find one that is not too far off from the prices that you are willing to purchase.
What ever you do PLEASE get one of the wonderful ladies here to authenticate it for you... before purchase... this will save you a lot of heartache and headache...
Good luck in your decision and welcome to the Chanel world!
Personally, I quite like the look of the vertical quilted bags, especially because they are vintage and not so widely available now. But, I also think you'll end up wanting to buy the classic jumbo later. So it's up to you to weigh up which you want more and now.
A quick look on eBay and there's not many vertical quilted bags to choose from, but $2k-ish doesn't seem unreasonable comparatively. But this, of course, depends on the condition of the bag. Be sure to post up a picture if you end up buying one!