A friend wants a cigar...

Aside from gifts and I'd explain why on those, I'd let them pick their own and I'd answer any questions they asked. Who am I to decide what they will or won't appreciate?

I've never had to deal with cigar mooches, so I'll cross that bridge if or when I get there. I never liked mooches when I smoked cigarettes, especially the regular repeat offenders. But more often than not, I gave them one anyway.

[macpappy]

I keep a humidor with a variety of singles just for cases like the four you mention. As I only keep 10 - 15 in this humidor and wind up replacing them about every 2 weeks I don't worry too much about the flavors blending.
With #1, I tell him to take a look and see if there is anything he would like to try but that I don't smoke his brand.

With #2, I tell him to take a look and to let me know if he doesn't see anything he likes. If this happens then I tell him what his higher end options are and I pull it out of my cooler.

With #3, the same unless I have something in mind that I think he would like.

#4, I just let them pick something from the humidor. It's only a cigar and I remember when I first started smoking cigars back in the 70s and I enjoyed the original Backwoods.