There’s no fantastic or ‘always’ answer to this question … it just depends. The best teacher is experience.. If someone was starting out with pipe tobacco smoking today, I’d recommend they hang out with Savinelli for a few pipes to get a sort of baseline — their KS size isn’t huge, really, but is adequate and they have some lovely designs. I am lusting after one of their Oceano pipes for instance. But my first was a Sav 606KS and the first is often a favorite.
I have several Savinelli Autographs, one McClary, some Ben Wades, a lovely Brigham or two, and 30 others. I would say that one of the mistakes I made was not checking true dimensions and trusting the photos … which of course can be enlarged. Not that a small bowl is a bad thing!
My son just returned from a vacation in Japan and bought Dad a lovely sandblasted Stanwell in a bent apple shape. I will treasure this.
My only real counsel would be to invest in a high quality block meerschaum at some point. Don’t go cheap on this — go to the Meerschaum Market, reach out to Burak, and get a high grade IMP Meerschaum level pipe. A meerschaum will always reflect the actual tobacco taste better than most briar or other wood pipes, and will not retain tobacco flavoring, and will always smoke ‘cooler’ than a briar. Over time a nice yellowing takes place which you will know is because of you. Not cheap means $350-400 USD, or more if you want a lot of intricate carving.
I mention this company (there are others, like say, Altinay, which are excellent) because on EBay etc you will see a cheaper meerschaum which is not block and has been enlarged and/or does not show the true dimensions. This is a noob mistake, and can be costly.