How to spot quality?

Fit and finish, drilling, overall visual balance.

Grain and curing of wood.

Depends on what you are looking for. Smoking functionality only or aesthetics too.

It depends on what you're looking for. If it appears on some of the major retailer sites, you may find a handful of bad eggs, but mostly good pipes. I have cobs and most grades up through four figure artisans. A $50 Rossi smokes just as good as an $800 commission. Just depends on what you like and what you're willing to spend. The last couple of years before I quit buying though I would just buy estates and restore them for less than $30/pipe.

Wilson's a part of Gubbels who also makes the Big Ben pipes and Al Pascia's curvy line. I've got an old Big Ben dromedary that's a joy to smoke. For packing, give these a go.
https://youtu.be/OP5MjK8KS7U

I have found that pipes that feel lighter than they “should” tend to smoke better for me. By this I mean that when you go to pick up a pipe, your mind has an idea of what that pipe should weigh and I’ve found lighter pipes with drier wood smoke better.

Firstly, if you haven't got your drying/packing/breathing game down yet, you won't be getting good smokes from a $5 cob or a $500 customized Briar. My advice is to always work on that first.
But we all know that the PAD struggle is real. Fit and finish are important obviously, but I like pipes with thicker walls. Once you have your mechanics of the pipe sorted, the rest is aesthetic.

My Stanwells all smoke good. They make some pipes that are relatively lightweight compared to their size and I like that. There is much love for Petersons and Savinellis so I assume they are good as well. I have one Peterson and it is a good pipe. Chacom also makes affordable pipes that are well crafted. I have two and they are among my favorites.

One thing to consider is the shape of the chamber. Several members seem to prefer a conical, dublin-type chamber. Others like a wider, shallower apple-type chamber. I find the billiard-type straight drilled chamber works best for me most of the time.

In my opinion, you need to handle a pipe to know if it is really quality, regardless of make. So if you buy online, make sure you can return it unsmoked if there is something you don't like. Of course smoking it is the biggest test, but even then there will probably be a break in period. Look for these things:
Clean fit at finish- no gaps, uneven drill holes, etc.

The stem hole should hit the exact bottom or slightly below the chamber of the bowl

The draw of the pipe should be wide open and feel like sucking air through a straw

The pipe should be light for its size. I don't own any pipes that way more than 50 grams
Other factors are more personal preference. Even though there are nice hand cut acrylic stems out there, I pretty much just like vulcanite as the softer material is much easier to clench. I would caution you against going crazy buying pipes. They DONT accrue in value with a few exceptions, and of course you can only smoke one at a time. It helps to look for lightly used estate pipes, sometimes you can get a nice hand made vintage Ashton or Comoy for the same price as a new Savinelli. Those older pipes are easier to resell if you don't like them too. Good luck.

One more thing to consider: why do you buy a particular pipe? If you are looking for a good smoker and don't care about particular details, I guess your question would be pointless. Assuming that you are looking for a good looking smoker, you could find a variety of fine pipes that can fit any budget from $50 to a couple of hundred. Buying estates that you restore can yield very satisfying results, both in appearance and performance. If you are looking for collectible value/custom made pipes, I am not the right person to be giving advice.
Personally, when I look at a pipe I appreciate the shape - how that would fill my rotation, or collection, or simply how much I like that particular shape (I have a fondness for bulldogs for example). I have started to stay away from pipes that are not stamped with some more or less known manufacturers, as I have found out that while they may smoke well I don't have the room to store whatever I can get my hands on. Every so often I may buy a basket pipe if it winks at me hard enough. I guess quality is something that I just appreciate on the spot, after seeing some pipes. I like a nice interesting grain in a smooth pipe, and I don't shy away from rusticated either. In estates I like my stem logos and briar stamps to be in good shape, and I also examine stems for cracks or past repairs. With a bit of effort, and sometimes aid, any pipe can be restored to its former glory. If new, I don't buy pipes that have chips if smooth, or if the stem-shank fit is not good. Depending on price, I do look for finer detail work on your more expensive pipes. At the end of the day I am convinced that pipes that are true pieces of art cost more money than I can afford, and I am fine with that.
For the $200-$300 budget you mentioned I would't worry too much about quality. Unless an issue that quality control didn't catch, expensive factory pipes nowadays live up to the price.

Buying pipes is like buying horses, boats, or automobiles. You have to look at a lot of them so you can spot quality when you see it. This means looking at them in person, for a long time, when you're not actually buying anything, so you are fully attuned to what your seeing and not to your longings. Look at quite a few pipes priced much more than you ever plan to pay, to see what those are, and what's so great about them. Pipe shows are great for handling pipes and examining them. Pipe shops, pipe clubs. After conducting your own preliminary course in pipes, I'd choose a very modest price level and shop that, the best pipe you can get for fifty, eighty, or a hundred bucks, based on your knowledge of pipes that cost hundreds. Then you have the option of staying at the affordable level or ratcheting up, but you'll have an educated feel for what you're seeing. Learn about filters, shapes, materials, stems and bits, brands and sub-brands, new and estate pipes, and different sizes ... and much more.

Buying pipes is like buying horses, boats, or automobiles. You have to look at a lot of them so you can spot quality when you see it. This means looking at them in person, for a long time, when you're not actually buying anything, so you are fully attuned to what your seeing and not to your longings. Look at quite a few pipes priced much more than you ever plan to pay, to see what those are, and what's so great about them. Pipe shows are great for handling pipes and examining them, as are pipe shops, pipe clubs. After conducting your own preliminary course in pipes, I'd choose a very modest price level and shop that, the best pipe you can get for fifty, eighty, or a hundred bucks, based on your knowledge of pipes that cost hundreds. Then you have the option of staying at the affordable level or ratcheting up, but you'll have an educated feel for what you're seeing. Learn about filters, shapes, materials, stems and bits, brands and sub-brands, new and estate pipes, and different sizes ... and much more. Talk to pipe smokers and see what they know, but evaluate what you're hearing. Everyone has their own subjective take, and a lot of it is deeply felt and ardent, but not necessarily factual nor commonly shared. But you'll learn a lot, if you process what you're hearing.

Edit on my last post- "i can't afford" when speaking of "pieces of art pipes".

I like Hiplains' post - pipe to pipe, you can assess certain fundamentals, and it's not that money makes them happen, but... at a certain price point, they are more likely to exist or be done correctly.
I think that price point is, roughly, 300 bucks. That's where pipes get really good, and separate themselves from the 150-200 dollar pipes.
Example?
Well, heck, I bought a 200 dollar "Punto Oro" Savinelli - this is their flagship pipe. And it's... okay. Not great, but okay. But gosh the heel gets hot. Why? A little experimentation, and ... great Scott... the drilling is so crooked that there is literally 1/32" of briar in the heel!

I would have been better putting that 200 bucks into a Castello, or a Ryan Alden. Even the Sasquatch cuts a better piece than that, I mean... jesus.
I see a vast difference in my "good" Petersons (140th anniversary, Sherlock Holmes, etc) than the "run of the mill" ones that are 100 bucks cheaper. And a vast difference between a bottom-grade Castello (at say, 300 bucks out of Italy) and a top grade Savinelli. I know many smokers who detect no difference at all. So be it. I sell pipes daily to people who do see and care about that difference.
As to "seeing quality"... I'm honestly not sure a new pipe smoker can do so. More likely you'll be dazzled by fancy bangles and shiny finishes, and things like the particular cut or particular bend of a stem will remain a little mysterious - and this isn't to offer insult, it's just the simple truth; it takes some study to learn these things.
I think most pipes at 150-200 bucks are about equivalent - you buy a Peterson, a Savinelli, a Stanwell.. whatever. But move up one notch on that totem pole, move to hand-made pipes made by people who care... and suddenly you've got a real winner. YMMV. I bought a Castello some.. 6 or 7 years back I guess, thinking "Good Lord this is expensive". I have a few more of them now, having proven themselves to be dead reliable as compared to other "big brand" pipes. Artisan-made pipes are another thing entirely, and there are lots of very good ones to be had, but again, 300 bucks is a sort of starting point for a very good pipe with all the details taken care of.

"Punto Oro" Savinelli - this is their flagship pipe.

Click to expand...

What about the Giubileo d'Oro line?