First pipe

Grats on the new pipe!

I found Virginias in my pipes smoke hotter so I needed to really make a conscious effort to go slow or they would get kind pretty crappy. I did find them pretty enjoyable when I could muster the discipline to slow it down, but pretty light in flavor.
I don't believe you'll need the tar cleaner ever time. I usually just swab the pipe with a pipe cleaner or 2 through the shank and loop it and gently wipe the bowl. I do from time to time also soak a pipe cleaner in high % rubbing alcohol to swab the shank out. Only doing a hardcore cleaning when needed.

Going from cigars to pipes I haven't found too many aromatics terribly enjoyable, but I have quite a few. Usually people consider aromatics much more goopy and they impart more ghosting in a pipe therefore using separate pipes for aro's and others is usually the preferred method. I have quite a few briars, but I found if only going from one bowl to another there wouldn't be much if any ghosting involved, it's when you do multiple bowls of the same type that problems may arise. Of course there are always exceptions.

Chris