Welcome from Florida. I would recommend you get a real briar pipe to begin your journey. I started with a Savinelli Linea Piu 5 Apple shaped. No filters, no adapters just a nice wide open shank airway so you can get a nice dry flavorful smoke. I make sure all my pipes have at least a 4.0-4.5 shank opening. If you are buying on line as the seller to check the opening and let them know that it i s a deal breaker if any pipe is less than 4.0.
Read all you can, look at video's but you have to start with a good quality pipe. If you don't get a good pipe, then how will you know if you got a lemon down the road. My first was the Savinelli, my second was a George Jensen that was a piece of crap. It burned hotter than any pipe ever should. But what if, the Jensen was my first pipe, I probably would have given up pretty quickly.
You need a baseline pipe. You will need to learn what type of humidity do you need for certain blends, they are not all the same. I smoke flake tobacco 99% of the time. I prefer my flakes to be a bit moist as the slower I smoke the more flavor I get. When I take a flake and fold and stuff it into one of my flake pipes. I get a much cooler,slower,drier and more flavorful smoke. There are videos and articles all over the web on how to fold and stuff or cube cut or rub out your flakes. I would recommend cube cutting for a beginner. I have never recommended a cob for a first pipe. Lots of people do but I am not one of those people. I smoke briar pipes only. I have a strict criteria for any pipe that I buy.
I like a pipe that has a 2.0" bowl height, a 1.5 inside bowl depth, .75-.83 inside bowl width. 5.0-6.5 pipe length. My criteria keeps going but for now this will suffice.
Patience is now your friend, don't give up before the miracle happens. Hell you might get lucky and hit gold on the first bowlful.
Since you were a cigar guy, I would go with Peterson Navy Rolls which is the old Dunhill Deluxe Navy Rolls, and a tin of Capstan Blue flake as it is smooth, easy to smoke, ready to roll right out of the tin with no extra drying needed. I would go for one of each and see how a straight Virginia )Capstan) and a Virginia/Perique blend smokes like.
I never recommend aromatics to start with I say go big or go home. These two blends with a good pipe
