I started with pipes and have been smoking them a little over three years now. I only started seriously getting into cigars since last June. I love both, but for different reasons.
Pipes are highly individualistic and personal. For me, they transmute baser things, such as loneliness and confusion, into solitude and clarity. A good cigar can approach achieving the same, but not to the same degree as pipe smoking. I've multiple pipes and blends to choose from, and can even customize a blend as I see fit should the mood strike. It carries a more ritualistic and personal approach. I can and often do smoke my pipe in company, but it is something I prefer to do unbothered. Pipe smoke is also generally just way more pleasant than cigar smoke, which is important, because with due diligence, I can safely smoke inside without damaging the walls or stinking up the place. With cigars, that is harder to do, at least in my experience.
Cigars, however, encourage sociability in me. Giving someone my pipe would be like letting them use my toothbrush, but I can give a friend or stranger a cigar without issue, and I've had great experiences of fellowship thanks to the sharing of good cigars. Smoking a cigar alone is also a great experience, and they are less fussy when dealing with inclement weather than pipes. They also have an uniquely robust profile. My humidor usually has around 20-30 sticks in it at any given time. The cost of good cigars does creep up, however; so I do budget for it appropriately, whereas a tin of pipe tobacco is less than $20 and will last me a long time, because I smoke my pipe no more than twice daily on average. If not for PAD, pipe smoking would be a fairly affordable hobby, but with cigars, I must budget. As such, I may smoke 1-2 cigars a week, if that (I tend smoke fewer cigars when cold weather sets in).
Love both and would like to continue enjoying both for as long as I can. I prefer pipes slightly, but both give me what I want.