My pipe tobacco choices are more seasonal than my cigar choices. Cigar choices are situational. Short time vs long time, activity while smoking, am I on call, etc… I do tend to prefer maduro wrappers in the fall for some reason.
With pipe baccy, I tend towards burley blends in the spring, VaPers in the summer, both in the fall with an occasional latakia blend (must be the smoky thing), and just about anything in the winter when I am either inside or shoveling snow outside. Snow shoveling requires either a quality aromatic or VaPer.