would buy one box of something that would fit into my rotation. Keep the rest for a deal when it happens.
I have depth in my regular sticks, and really do not need anything in that category.
You need a plan to maximize your 500.00...... Don't give it to the pressure of spending all of it in one go.
Decide what you will do with the cigars, age and try occasionally, long term age, smoke now.
This should determine what to buy.
I would avoid Cohiba, too hard to keep your hands off, and they really need 5 years.
If you can find some aged stock, spend a bit more and accelerate your learning curve.
Samplers would be another way, broaden your knowledge of brands, and then pick.
And, I would stay in the sub 50 ring gauge category until you have tried most brands and have an idea of your favorites.