Being the owner of a couple, I would buy in the following order:
1) the Chanel - timeless and a great investment
2) The Spy because I just love it.
3) The Edith
4) The Paddington
5) the B Bag or Gaucho
And may I add to your options the Balenciaga? I love them. And the Mulberry Roxanne. Two personal favorites of mine.
You need to consider what kind of bag you want though - trendy or timeless? If you are getting your first "big" bag I would go for timeless, personally. That's why I said Chanel. The gaucho and b bag are cute but they are super trendy and I predict that they will over saturate the market within a season or two. However, the Chanel never goes out of style. If you want a super trendy "it" bag, do you want a tried and tested one like the Paddington or do you want a "fresh" one for spring like the Edith or the Gaucho? I think the Edith may be a good investment for a new "it" bag because it is understated and not over the top. The leather on Chloe is spectacular and it looks easier to carry than the Paddington. Plus, the gaucho, although cute, seems very trendy to me, so much so that I wonder if it will last past one season.
Let me know what you decide and good luck!