Introductory - H. Upmann Majestic, Hoyo de Monterrey Palmas Extra, Hoyo de Monterrey Petit Robusto. All are a smaller size, all are pretty inoffensive tastewise, and none break the bank.
Daily driver - Cuban custom rolls have been my daily drivers recently, I really enjoy double coronas and larger format cigars in the evening when I have 2 hours to myself.
Impress your guest - I have two tricks up my sleeve here, the first is a regional edition from whereever they are from or their ancestors. I have a lovely box of SLR Pacificos I have been handing out to start a discussion around the qualities of aged cuban tobacco.
Friday night smoke - Double corona for sure, normally a lusitania or a large format/posh regional cigar.
The special occasion - Gran Reserva, for wedding anniversary is from one of my few boxes with my anniverary month/year, and sometimes I'll just mark the calender wherein the special occasion is smoking and reviewing the cigar in question, especially vintage smokes.