My first cologne purchase in 20 years was last Christmas, and it was HM EDT. It was sweet (less so than the EDP, which does smell different and has a chocolate-cherry flavor), and it has a nice fresh citrusy smell which my wife liked a lot, with a vanilla finish ... a very modern fragrance. Since then I have gotten Guerlain Vetiver, L'Instant, Terre D'Hermes, Chanel Pour Homme and Creed Himalaya, so this can be an expensive (but fun) habit.
As to application, that's really a personal preference. You want to go easy as your nose will get used to the smell and you will then think you do not have a lot on when in fact you do. You dont want to be intrusive. One mistake a lot of newbies make is, after they apply the juice for a few days, their nose is less sensitive and they think they haven't applied enough, so they spray more and stink out their family and friends. I personally spray two half sprays on either side of my neck and one half spray on each wrist. The HM atomizer, or at least the one on my bottle, seems to kick out a lot of juice. To me, the trick is to have enough on so that someone notices when they are around you for a while but not so much as it is immediately noticeable. For that reason, it is better to apply a little every so often. Since I can only apply it on the way to work in the morning for the entire day, I will put a little more on in the morning. I hope that makes sense. You can use a little more in the evening when you are in a social setting. I think there's a lot of good advice on websites like men.com and gq.com on applying cologne.
I would not recommend buying blind until you are better at identifying what you like and what you dont like. Spend some time at Nordstroms and Macy's, for instance, spray some samples on cards and then read about them on Basenotes (especially when the review database is back online). Then go to a Neiman Marcus, for instance, and try out the Creeds (unless Nordstrom carries those in your area), but take it slow. I have learned that many fragrances are an "acquired taste." This board can be very helpful, but there's no substitute for doing your homework.
Hope this helps and good luck!