First of all, welcome to the hobby. Looks like you're down the right track, by doing a lot of reading in various places, this forum being one of the best, but as noted above, there are many rabbit holes. In the final analysis, your own tastes will be the best guide that you can have, but in the process of developing that good sense, there are many pathways to take, some of which will work for you and some of which won't. As we frequently say in this hobby, de gustibus non est disputandum.. This means that you will come to appreciate certain pipes styles, certain types of pipes, certain broad tobacco styles, and within that certain specific tobaccos, and so on and so forth. You are your own person, and no one can tell you want to like or not like.
This being said, there are certain fixed rules that I give to every new pipe smoker, as follows:
1. Your tobacco should always be drier than you think it should be.
2. Your tobacco should always be packed looser than you think it should be.
3. You should always smoke your pipe slower then you think you should; i.e., sip, don't puff.
When it comes to pipes, there are two broad styles: briars and corncobs. First, look at corncobs – you won't be disappointed. There are two preeminent brands, Missouri Meerschaum, and Old Dominion. They taste quite different, but provide superlative smokes. And don't think for a moment that you look like a rustic smoking one of these. Before my retirement I wore a suit and white shirt to my office every day, and I have never been ashamed to be seen with a corn cob sticking out of my mouth. Some individuals smoke nothing but corncobs, but every pipe smoker should have a couple of these in his inventory.
As to briars, the costs run all the way from a $20 pipe available in most drug stores (except CVS,) to the thousands of dollars, and you're the best judge of your own financial means. However, some drugstore pipes have yielded superlatives smokes, and keep in mind that a $1000 pipe won't smoke any better than a $500 pipe, or even many pipes selling for a good bit less. At that rarified atmosphere you're paying for artistry, not the quality of the smoke. Among the factory made pipes these names stand out: Savinelli, Stanwell, and Peterson, excellent pipes by and large. Among artisanal pipes, the sky's the limit.
Tobacco's come in three broad categories: Virginia, English/Balkan, and aromatics. Let's look at aromatics, tobaccos to which something has been added to increase/enhance/change the flavor and aroma, often for the benefit of achieving a particular room note, since the smoker himself usually can't taste the flavoring. Here I would recommend 1-Q, RLP-6, for a good, general start, and Molto Dolce for something at the extreme end, but truly a heavenly smoke. Try any of these three, and at least you'll have a basis for comparison and further selections, of which there are more than you can probably do in a lifetime.
English/Balkan used to mean tobaccos which were governed under a particular British law that no longer exists, and which prohibited the addition of any flavoring ingredient to a tobacco. These tobaccos usually relied upon the addition of Latakia to the mix, providing a smoky, campfire-like aroma. I've smoked these for over 50 years and found them to be remarkably pleasant, although occasionally a bit pungent for the bystander. Balkan Sobranie, Black House, Nightcap and Early Morning Pipe are good places to start, and I would add Lane's HGL to that. Although it's regarded as a crossover type mix, it's remarkably mild and pleasant. Also, don't forget any of the Frog Morton blends.
Virginia tobaccos are often regarded as the choice for purists, although they, too, are not exempt from the addition of flavoring ingredients. Here again the field is wide, but some I like to recommend include Orlik's Golden Sliced, a Virginia/perique blend, Dunhill's Elizabethan, and Manhattan Afternoon, a virginia sweetened with just a touch of honey.
Start with these, and in a short time you'll develop your own palate and will be able to choose from amongst the literally thousands of pipe tobaccos out there.
Matches (wooden--never paper,) are the best way to light a pipe. Zippo makes lighters with a pipe insert, and these are good because they provide a flame at a relatively low temperature, although some find the aroma of the fuel itself to be offputting. Significantly higher up the temperature scale are the butane lighters which range from an inexpensive Bic, to lighters costing in the hundreds of dollars. Never use a torch lighter to light a pipe.
This is just some general information. You'll quickly develop your own preferences, and before long will be offering advice to other new pipe smokers. Again, welcome to the hobby.