The story:
I bought a pipe and some tobacco, and started on a journey that was quickly quashed as my wife laughed me out of continuing (she finds pipe smoking very uh, pompous.
Pipe smoking is definitely not pompous, much less so than cigar smoking. If you want to make a plebeian statement, get a corn cob pipe! I got a new MM Hobbit cob a few weeks ago, still haven't smoked it, but it does look very nice. I also own several others.
The biggest being I can load a bowl with an eye to time - which is a huge advantage when smoking in the winter.
Get some small pipes- estate pipes are good for this. I like Willard and Kaywoodie. They also make good out-and-about pipes as I don't need to carry pipe cleaners, I just wipe off the metal "stinger" and clean out the pipe every so often at home.
You can use mini Boveda 62 packets with pipe tobacco, it works very well with a larger container to keep the moisture just right. Humidrol clay buttons also work but you need to watch out for mold. For long term storage, mylar bags or mason jars are the way to go, short term - Tupperware pipe tobacco tins, heavy-duty zip-locks, and vinyl tobacco pouches are best.
If you use a filter pipe- I recommend Savinelli balsa filters. They work even in a Grabow pipe. If you smoke a Grabow without a filter, its doable but you'll get an extremely open draw.
What's up with this letting your pipe rest for a "couple" of days? Can I smoke two bowls in the same pipe in one day?
Yes, just make sure your pipe is fairly dry between smokes. I believe resting pipes for days is overrated, it was really an idea spawned by folks that wanted to sell more pipes. But nonetheless, most pipe smokers have a small rotation. Small is all you really need, you don't need dozens of pipes (like I do, but then I'm a collecting fool).
I have some metal pipes like Kirsten and Falcon. They don't really require rest, just maybe occasionally changing out the bowls.
Another thing you'll want are Long's Softy Pipe bits. They are kinder on the vulcanite stems and safer for your teeth when you clench the pipe. They cost about 2 dollars for a few of them.