Welcome to the boards from outside of Ottawa.

You're off to a good start with the newbie sampler.

As for whether it's better to start with a nice humidor or nice cigars, that depends, are you ok with having a tupperdor and some beads to store your nice cigars until you get that nice humidor? If you are that's the quickest way to get into it. In the end you probably will want that nice humidor. A tupperdor is just like a coolidor but on a smaller scale.

Personally, I started with a small cheap humidor and a coolidor, now I have a nice humidor and still have the coolidor but am looking at a bigger/another coolidor until I get the time/money to build a walkin humidor in my basement.

It's a slippery slope, some would call it a cliff.