Interesting topic.
Here's what I base purchases off of..
1. Ring Gauge - I'm a 48+ size. I know a lot of people here are long and skinny folks, sorry.
2. Length - I don't care, I figure length only comes in play when I have to consider the amount of time I have to enjoy a cigar.
3. Brand - Read this forum, you'll notice who you agree and disagree with very quickly. Then based off of who you agree with try what they are trying. Maybe even send them a PM and see what they like.
4. QTY - Buy samplers, then if you like what you smoked buy a box.
5. Notes - Take notes. Find flavors that you like or don't like and build off of that. I have an iphone with a notes app. I have pages of notes on there that I refer to each time I want a smoke.
6. Mood - In my opinion you need to have mood cigars. These are cigars that you want to either mourn with or celebrate with. These are either strong happy notes (flavors that you itch for, mine are coffee, toffee, dried fruit), or notes that put you into thought (mine are spice, nutmeg, pepper)
7. gamble - Many times a box of 25 will only produce 15 good cigars. that's okay, that's part of the fun. If you won every time you put your money on black it would get boring after a while... okay bad example...
In the end cigars are not for the struggling. I hate to sound like a prick, but the facts are the facts. However you mentioned that you're a student, that means you're busting your ass to become something. And there's no better way to reward yourself after busting your ass than to treat yourself to something you like.
So I'm going to end this long winded post on a challenge.
1. What type of student are you?
2. Where are you located?
3. Do you have a test or project due soon?
If you're in the same country as I am (for shipping reasons) and you get an "A" or 90% and above on your next project and you can prove it to me (scan results as a response to this post). I'll send you a celebration cigar.
Deal?