New Smoker.

Look up military mounts in Pipedia, and see how a military style pipe is constructed. The Peterson Irish Made Line of pipes have a military style mount, and are a good value. Many manufacturers make a military or army mount.

There are a gazillion pipemakers out there, and you can get a pipe in any price range that you want. GO for something that looks good to you, and jump in. I started out with a corncob and a Dr. Grabow, then moved up to Edwards pipes. Edwards, Peterson, Savinelli, Butz Choquin, Nording, all are good factory pipes with decent entry level prices. Briarworks Icarus and Neptune pipes are made here in the US, and the one I have is pretty nice. If you want to go better, then research some artisan pipe makers. There are dozens of them, and a hundred opinions of who is and isnt the best. This forum is full of them.

A good pipe shop should be willing to give you some help with the differences between Virginia, Perique, Burley, etc. FInding a pipe club in your area would be the best ticket.

Best thing to do, pick up a pipe, and start puffing!

Hello and welcome to the site!
I think you are off to a great start. I don't know what a Casillero pipe is, but you can never go wrong with Missouri Meerschaum CC pipes! Instead of diving in and blowing 2 years of tax returns on pipes (like me), you may want to just deca-down (instead of double) and get a bag of smokeable seconds from Missouri Meerschaum. They are a site sponsor and easily the most cost effective way to sample a bunch of tobaccos. Bag 'o Pipes Here
I like where your head is at sampling a lot of tobaccos. That should never end. As you move from Aromatics to other types of tobacco (English, Virginias, Virginia/Periques, etc) You will want to use fresh pipes so as to not muddle the flavor. There is where having a bag 'o cobbs will come in handy again.
Also, journalling what you like and don't like is a good idea. That said, if you don't like a tobacco, jar it up and try it again in 6 months and again at 1 year. This will mellow out the tobacco and/or your palate will adjust and you may find you like it.
With regards to tobacco. I liken it to food. You have your amber waves of grain types as your salad (Virginias). You have your smokey meats (Englishes and Orientals). And your have your desert tobaccos, like the 1-Q (Aromatics). There is literally a tobacco for every taste proclivity you possess. If not, mix some together and make one that is right for you.
Once you have found some good tobaccos and done some research on pipes, there are a great many site sponsored places to acquire them. If you want to tackle ebay, Pipestud is a great seller and has auctions go off every Saturday.
Without seeing the pipes at your local auction and getting the brand and condition, there is no way of knowing what you were looking at. If you can, during previews, you can post on here what brands you are looking at and do your best to gauge condition (will require a fair bit of research) and people where will get you a good estimate of value if they are online.
I have to get out of the office now. Again, welcome to the site!
Oh, and as a final note: If you start buying a bunch of 1-2 oz sample tobaccos in baggies to try out, invest in mylar bags on ebay or small mason jars if you are not going to use up your tobacco within a month or so. It will keep the flavor and is the best way to store baccy.
~Wyfbane

realfloop', welcome aboard. You can buy an excellent pipe new or used for $200, but you need to do a lot of homework, shop a lot without buying anything, and ask good questions here and elsewhere to get the most out of your purchase. Meantime, a few MM cobs wills serve nicely as you find your taste in tobaccos. Buy only small quantities, an ounce or two, even if you find something you really like, for a while. You may find a better blend the next day. Buying fewer pipes at higher prices is one good strategy. You won't get the variety of shapes and nations, but you should get excellent smokers with a touch of craft and history. It's easier to get a good new pipe, after researching them, but you won't get as much for your money. But more can go wrong with used pipes; you might want to stick with one of our sponsor retailers for used pipes, unless you are experienced with ebay. A disclaimer, I have stuck mostly with moderately or lower priced pipes, for more variety, but I think both ways of going are good, if you work at them.

Welcome aboard

If you have the $$$ to spend on expensive pipes, spend some time here and figure out what makes sense. Starting with a few cobs is never a bad idea, I agree. I would get two new Castello pipes for sure, if I had the $$$, but not in my budget, as they are $700 and $1,000 respectively. For that $$$ I am getting another single action .357 mag revolver, not a pipe. For around $100 +/- you can get a new/good pipe that will smoke real nice. I use and suggest Stanwell, Comoy, Chacom and Savinelli. Just got a new Savinelli Oscar Tiger Zulu for $108 to my door. Have a commission Zulu/Horn coming for $210.00. Made just like I want. I spent a couple few hundred dollars on some "Estate" pipes and most were real good deals. I have a herd of Missouri Meerschaum Cobs. I spent in excess of 200 hours of research when I got serious about all this and only then started to spend my $$$. Tobacco reviews is a great resource. I always look for the reviews of Pipestud and Jiminks, two members here, who have written around 2500 reviews between them. I had one briar pipe and many cobs for about 20 years and smoked Captain Black exclusively. That worked for me, and then I got sucked into all this, big time.

Welcome to the brotherhood.

I'd say you can't beat a nice Savinelli or Peterson.

Do you prefer straight ,half bent, full bent?

Try to decide with a cheaper pipe first like a good MM Cob.
Welcome and enjoy!

Hi realfloop,

The military stock conversion to pipe sounds intriguing, please include some pics when you can!

I recall many a military mount in the day......

Had a military mount once. Didn't work out - she got the house.

MSO489 gave you some very solid advice. I'd second everything he said.

I would guess "Castillero" is an attempt to play off the strength of the name "Castello", a very fine Italian pipe maker.

And I will add my standard advice: Smoke the best tobacco you can afford, in the best pipes you can afford.