First Time Smoking a Pipe Today: Some Questions

Welcome to the forum. OK, you've chosen 2 blends to try and I would not worry about smoking them in the same pipe as neither should drastically affect the other. The key to pipe smoking is packing and cadence.

Start with this video from James Foxx Tobacco in Dublin and watch the rest. nice short tips on how to do the art of pipe smoking. Good luck on your journey.
http://www.bing.com/videos/search?q=james+fox+pipe+videos&FORM=VIRE3#view=detail&mid=141516F30609D0B9D464141516F30609D0B9D464

Nothing wrong with smoking aros and nons in the same bowl. I've been doing it for fifty years. Some guys just prefer not to. To some smokers, the pipe is a ritual thing, others enjoy chasing blends just to experience the different tastes. Still others, I am one, mostly use the pipe as a nicotine delivery device. There is no one type of person who smokes a pipe.
Don't know what or where you've been reading but, letting a pipe cool before dumping accomplishes nothing. Do it all the time, especially when I only have one pipe out in the field. I reload and light up, bowl hot or cold.
Sorry to burst your bubble but, kids your age, especially in college, take up the pipe all the time. A good percentage simply drop the habit (Oh! So sorry, hobby) later.
There is no great learning curve to smoking a pipe, nothing mystical. Proper loading will come with experience. If you experience discomfort with a blend, don't smoke it.
Lots of other advice and tips will follow I'm sure. A lot of it will conflict as the pipe, if nothing else, is an individual thing.

Welcome to the hobby. In my experience it's not necessary to cool the pipe before dumping out ash. As far as finishing the pipe tomorrow that shouldn't be a problem.
As far as not getting sick, slow and steady wins the race. Smoking 10 to 15 minutes at a time is a great idea. As is having something with you to drink.
Some tobaccos pack a lot of nicotine;consider sticking with low-nic options. It seems like you are on the right track so enjoy!

Welcome aboard, probester. You've chosen two tobacco blends that are relatively mild in terms of nicotine, so I wouldn't worry about throwing up. They are both aromatics, really, though the Captain Black is obviously more aggressively flavored. So I wouldn't worry about smoking them in the same pipe. If you enjoy pipe smoking and stay with it, the time will come when your tastes broaden into tobacco blend genres disparate enough that you will want to dedicate pipes to each style (some, and I am one, dedicate pipes to specific blends within the style). But for now, don't worry about it. There's a whole universe of fascinating flavors and aromas waiting for you. Just enjoy the ride and don't hesitate to ask questions along the way.

There is no problem with finishing the bowl tomorrow. You probably don't want to leave tobacco in there for days on end, the pipe needs to dry out, but overnight is no big deal. You can smoke aro's and non-aro's in the same pipe. No problem. Sometimes some flavor from the previous bowl carries over to the next bowl. Some hate that and dedicate certain pipes to certain tobacco blends expressly to avoid that. I think that most of us don't dedicate pipes. Though it does occur to me that this is a good excuse to rationalize buying additional pipes. I don't mind a little flavor carry over. Sometimes, I quite like it.
Smoke slowly and don't inhale. Roll the smoke around in your mouth and then exhale. Don't overdo it at first. Also, you can pack half a bowl -- you don't need to fill it to the top. As you become accustomed to it and want to smoke for longer, you can fill the bowl more.
No need to let your pipe cool down before dumping the ash. Some will tell you to let your pipe cool down before removing the stem. Make sure you have pipe cleaners and use them religiously. A clean pipe is a good smoking pipe.
If you like Captain Black, you might wish to try, next time you order tobacco, some Lane 1Q, Lane RLP or Lane BCA. Lane makes Captain Black and these are similar, but the general consensus seems to be that these are "better" blends.
I'd also recommend that you try the Carter Hall a few more times. First impressions are not always the thing and after a few tries you may find that you like it.

The only thing I'll add, probester, is that Grabow uses an inner bowl coating that imparts a fairly noticeable taste for the first several bowls.
If you're enjoying the taste now, it will only get better as you burn off that coating.

I would simply not use the filter. If you are adamant about using it though, dump the filter every 2-3 bowls. Btw, I was 17 when I took up a pipe, and that was 24 years ago.

YouTube videos? If I were in a "slow smoking" competition I might smoke that slow.
Do as I did, experiment with your pipes. I didn't have a mentor, as it were, either.
If you pay a bit of attention you'll quickly discover what works with regard to loading. I, personally, load a bit in the bowl, tamp lightly with my finger, rotating the digit a bit as I press to nest the tobacco a bit. The next bit of blend is tamped a bit tighter. Each additional scoop of tobacco, I usually load from a roll up, is tamped wee bit tighter than the previous, always with a twisting motion until the bowl is filled. A large bowl may need four layers, or it may take only three. I just push in the blend, tamp and twist until full.
I don't carefully measure or visually judge the amount of tobacco when loading. The initial bit is very small though maybe a1/4 of an inch in the bowl after being tamped. A little less, a little more, whatever feels right from experience. When learning what works, test each layer with a slow draw, I find I like a little resistance when I smoke on the pipe. I do not want the resistance of say a thick malted through a straw, more like a "brown cow" (root beer float) where the ice cream has melted to mix with the beverage. So, let the draw tighten as you layer the blend into the bowl. No resistance in the first layer and gradually, very gradually increase it by tamping a bit tighter as you go. It'll soon become second nature.
I haven't consciously thought about loading in many years, I just do it. And, you get immediate feedback if you've messed it up when you take the first draw and you have to nearly suck your lungs out into the pipe to get the flame to lay into the tobacco. Then it is, dig it out and start over time.
This is why reading or watching different techniques is a tough way to learn, hard to describe or visualize. The slowly fading away brick and mortars were a great place to learn loading, rate and experimenting with blends. Immediate gratification could be achieved if the person running the shop was pipe smoker himself. Now? Now it is find an experienced smoker or, teach yourself and seek advice, much of which will be conflicting or confusing.
With regard to smoking rate, mine varies. If I am driving a chainsaw I can go through a bowl pretty darned fast when working hard. A bit slower when behind the camera, a bit more when lugging big glass, tripods and the like up a hillside. If I'm sitting at home in the evening with a book and a beverage I sometimes go 45 minutes to way above an hour. I sometimes need to relight if the book is really good and I forget I've got a pipe in my mouth.
There are very few "must dos" or "only ways" in the pipe. Maybe only two, you do need the flammable material and the pipe. After that, what ever works for you. Just don't let the learning process make it a stressful process. Enjoy the time learning.

The Omega pipe you have is a great starter pipe. I have four and still smoke them frequently. The way this particular pipe is made, you'll be fine with emptying the bowl and removing the stem while it's still warm. Never do this with a push stem pipe.
I wouldn't leave the unsmoked tobacco in the pipe for more than a couple hours if you're planning on finishing it. Just dump it and light a fresh bowl for your next smoke. Leaving a half smoked bowl overnight can turn your pipe sour.
Welcome aboard.

The only thing I'll add, probester, is that Grabow uses an inner bowl coating that imparts a fairly noticeable taste for the first several bowls...

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To put it mildly...
I really like my Grabows but, yes, they have a nasty bowl coating that needs to be burned off. Bear that in mind when gauging whether this hobby is for you. After those first several break-in bowls, you'll get much more flavor and less heat from your tobacco.

Practice, practice, practice. As Warren said, experiment with your pipes. Experiment with your tobaccos. This hobby is a never-ending world of experimentation. Don't think you'll like a cob? Try one anyway. Don't think you'll like a meer? Try one anyway. Think Lakelands sound gross? Screw it, buy one and give it a whirl. It might wind up being one of your favorites. Smoke fast, smoke slow. What works for you will manifest itself. This hobby is like a fingerprint-unique to each individual. Pack loose, pack tight. Whatever works for you is the "right way to do it". There is a lot a lot of great advice on this forum, but none of it is one size fits all. Use what works for you, and disregard the rest. The important part is the enjoyment. Welcome to the fold.

Great post!

Warren has unloaded some fine wisdom here above... especially what works for you. Try it out, experiment, waste some tobacco in the process. Puff too fast...get loopy, find your limits, your comfort zone. IF you think you packed it too loose, pack it tighter...repeat with different variables. This is why it is both a hobby and a habit, neither are mutually exclusive. I guess until like Warren pointed out you do it in the dark without thinking about it and wonder how that pipe got in your gob...then it's a habit.

What works for you will manifest itself.

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Unless you fail to achieve what works, hence the concept of persistence in the face of 'failure'. Most of us who have succeeded, have failed our fair share, but as this forum attests, there's gold in them thar hills.