At that price, you can try all but the very best cigars.
If you want cheap, you can still get pretty good cigars, especially smaller ones, in the $1-$3 range. But if you want something that looks good on the golf course, get at least the Robusto or Toro size.
The online retailers sell samplers, with a humidor. If the cigar is very strong, just get a sense of it. No inhaling.
Carlos Torano 1916
Indian Tabac Super Fuerte
Padilla
Fonseca
CAO Brazilia/Criollo
Padron
Rocky Patel Vintage/Juniors