Hello, ssgtusmc30
Great to have you, and welcome!!!
A couple of things that I've learned the hard way:
1. Start with a good estate pipe from a trusted source.
New Petes and Stanwells and Savinelli's sure look good (and cost more new) but they can take FOREVER to get broken in and start smoking sweet, in my experience. But most of my estates, from these brands and others, smoked great from the first or second bowl.
A well-broken in estate pipe that's been cleaned and sanitized will serve you well. You'll save money, and if you don't like it, chances are you can sell it on eBay for about what you bought it for.
2. You will have to experiment A LOT to find out what you like, especially when you factor in all the different options of tobaccos. What will happen is that sometime (hopefully soon), you'll have that "magical smoke." And who knows what factors contributed? The pipe shape, the pipe wood, the tobacco, the temperature, the company you kept, what you had for dinner, the room or atmosphere you're in......who knows? But you will spend many other smoking sessions trying to replicate that smoke. Much of the time you'll just be left with the memory. But that's part of the fun.
Size alone can be daunting: Some people collect GIANT pipes and some collect well-made tiny pipes. Part of this is an unexplained attraction, but part is also figuring out where you can smoke and what you'll be doing when you do. For instance, will you be driving or sitting in your favorite chair reading. Very different pipes are required!
3. Don't believe the hype. This applies to both tobacco and to pipes. From hanging out on the boards here and checking out other sites, you'll start to see what the flavors of the month (in the pipe-smoking community, it's more like flavor of the year-we move slower) are and you'll be tempted to follow the herd like one of my Jr. High kids because that's what people do-especially when they're new to something. THIS IS PERFECTLY NORMAL. However, don't be afraid to admit it to yourself when something just isn't for you--even if everyone else and their dog says it's the greatest thing ever. I've tried a dozen different times to get into Dunhill 965, and I don't enjoy it at all. I do love me some Nightcap though and even (GASP) the occasional quality aromatic. You've only got so many days and so many pipes and so many bowls on this earth. Don't waste them. And for God's sake, don't sell a good-smoking pipe just because it isn't as pretty or hyped as another. At the very least, give it to a good friend.