Jicky is purest poetry. I wandered around in a reverie when I first tried it. Love/hate - which is, after all, the essence of profoundest enamourment, and romantic confusion. You really must sample this before daring to buy it, though, as its civet may shock and dismay. But it really is a potentially moving fragrance; if you can enjoy it, I would vote for this first.
Cologne du Parfumeur is a very pleasant eau indeed. Very natural smelling, and a gorgeous orange blossom note. Not innovative, but it does what it does really well. In the 100 dollar price bracket - assuming you live in one of the countries enjoying such low prices (though there is always online) - it can be safely recommended. I have heard that Wasser (groomed as the future custodian of Guerlain, or something like that) created this as part of a tradition of each 'master perfumer' creating an eau de cologne to celebrate their acquisition of that high post.
L'Heure Bleue - I'm selective when it comes to anisic flowers, as they develop strangely on my skin. But I would prefer this to Habit Rouge, which has a creamy/citrusy/resiny accord that frankly strikes me as bizarre.
L'Instant - a good gourmand. True that it is not one of the classic Guerlains, though. But it is very wearable.
Actually, if you can get Arsen Lupin, Dandy, that's just wonderful. If you want just one of the truly classic Guerlains, it really needs to have 'guerlinade' in the drydown - that being the house's signature accord.