As a relative noob - I only have about 46 years - I'd say you're off to a good start by seeking info. There's been a lot of good info given to you, including "don't overthink it".
There are a number of methods to test out and as you go along, you'll find those that work well for you. No one method of packing works equally well with all types of tobacco. Time, patience, and experience are your best teachers.
You have a number of good resources at your disposal as have been mentioned above, articles at P&C, Pipedia, PipePhil, this and other pipe forums. Less reliable, but occasionally supplying good info are youtube videos. There are some interesting books on the subject published by
Briar Books Press Pipe shows can be a great way to become familiar with pipes, tobaccos, and the lore of pipe smoking while meeting fellow enthusiasts.
It's a never ending universe of pipes, tobaccos, lore, myth, history, and plain old BS.
At its core, pipe smoking is just the simple act of putting some tobacco in a pipe, setting fire to it and sucking in the smoke. But getting the most pleasure and flavor from the experience comes from understanding the best ways to do this. Again, time and experience are your best teachers.
I can share some of what works for me, with the understanding that it may, or may not, work for you. The other truth of the pipe smoking community is that there is little consensus about anything. Pipe smokers are often contrarian.
The best blends in any category:
There is no such thing. What I like and what someone else likes can be very different. I have gagged on more highly touted stink weed than I care to admit. Trying out some different types of blends will point you in a direction
for now. But chances are good that your tastes will change, and change again as you continue. One suggestion is that you check out some of the samplers available at P&C. You'll get to try several blends of each type, which will give you a good picture of that flavor profile of that type.
Expensive Briar -
Not necessary. Perfectly good briars can be found for a modest cost. Savinelli, Petersen, Stanwell, and others offer good entry level pipes. Do avoid cheap lacquered "basket" pipes. Estates are a good option, but I would avoid eBay until you are experienced as the offerings there are "variable" and you can easily become road kill. Better to go to your B&M, or try online dealers like Pulvers Briar, Briar Blues, Walker Briar Works, or Smoking Pipes.
But you can also completely avoid the expense for now and pick up some cobs. A great many experienced smokers, including some with impressive collections of expensive briars, smoke cobs because they deliver a good smoke for a minimal price. Thus you can devote more of your budget to testing out tobaccos.
Drying:
Some brands of tobacco, like Hearth and Home, are tinned at their optimal moisture level for producing the most flavor. Most tobaccos are packed with excess moisture and need a bit of drying out. How much drying out depends on the individual blend. My metric is that the tobacco feel dry to the touch when squeezed, but still be pliable. If it gets completely dried out, some flavor is lost. If the tobacco is too wet, some flavor is lost. Experience with your favorite blends will guide you to the best result.
Packing:
There are a lot of ways to pack a pipe and they all more or less work. Some work better with one form of tobacco than another. Gravity feeding works with cubed flakes. Three step packing works with ribbon cuts. My usual method is the "index finger" method, whereby I place my pipe in my pouch, lightly stuff a couple of layers of tobacco in it. Tamp it down lightly with said index finger, and light up the result. However you do it, the result should be lightly firm and stringy, and not interfere with the draw.
Lighting:
Some people employ a "charring light" to create an insulating layer of ash over the top of the tobacco. Char the top layer of tobacco and lightly tamp it down, then relight. Other people dispense with this entirely. I sometimes perform a charring light and other times don't. Depends on the blend.
Puffing:
Puff to get the pipe going, or to keep the coal from going out. Otherwise, you sip the tobacco, like you're sipping scotch.
Cadence:
You get the best flavor when the tobacco is simmering around the coal. It's not about getting huge billowing clouds of smoke, unless you're into cremating pipes and cremating tobacco. So the "art" of smoking, if there is such a thing, is to smoke slowly enough so that the tobaccos simmer and give up their flavors with the minimum heat possible. Practice and patience apply here.
Relights:
There is a theory that relighting a pipe is a sign of poor technique. This is crap. If your pipe goes out, relight it. There is no award for smoking a bowl without a relight. No brass bands or ticker tape parades will be offered to you for smoking with out relighting. The goal is to relax and enjoy the flavors. Otherwise, why bother?
Smoking to the bottom of the bowl is important:
This is also crap. Smoke what portion of the tobacco tastes good to you. If it stops tasting good, toss it out. Besides, trying to burn every last shred of tobacco in the bowl requires a lot of heat at the bottom of the bowl and that can eventually damage your pipe. It's good if the pipe is dry when you toss out the last bit, but that's not always possible with aromatics.
Tobacco cross talk:
It's advisable to smoke similar types of tobacco blends in a given bowl. Latakia and oriental tobaccos leave their scent in the chamber and will ghost a blend of a different type. Use one pipe for Virginias or Va/Pers. Use another for aromatics. Use another for English/Balkan/Oriental types.
Cleaning:
After a smoke, run a pipe cleaner or three through the airway to sop up moisture, oils, tar, etc so that it doesn't build up and spoil the taste of the next bowl. Wipe the walls of the chamber with a couple of doubled over pipe cleaners to reduce residue. At the end of a days use, clean your pipe.
Those are my suggestions, based on what has worked for me. Others will have different ideas based on their experience. Response to the flavors in a blend varies from person to person.
Just keep experimenting and learning. And, ask questions.