Hehehe

Prepare for your humidors to get neglected. lol

I'll echo some of what is already mentioned.
Cobs are indeed a good place to start. If you quickly realize that you like it, you can get an entry level briar pipe in the $30 range. Dr. Grabows are in that range and all 3 that I have smoke great.

As far as tobaccos, try a variety. As mentioned the NST is a great place to do this. It is where I got my introduction to many different types of blends.

Know that there is a bit of a learning curve with pipes. Packing a pipe properly will take a few tries more than likely.

Welcome to the slippery slope.