On the Padron tip, the '64 maduro exclusivo is my favorite, and will not break your bank at $11 a stick. Also, lasts a good 1.5 hours, depending on your puffing frequency. That would be my "island" cigar of choice. As has been said, the thousands line is a fantastic choice and the best bang for your buck. Had a 4000 maduro churchill gifted to me by my buddies at my local b&m recently, and it was superb.
Any of the Undercrowns, great value and usually can get 5 packs for $5 to $6 bucks per stick on cigar monster. My favorite is the corona doble. They also do not require the forfeiture of your firstborn child and wallet, as many of the liga privada line does.
Also, any of the My Father line by Pepin Garcia are winners, but a couple of my absolute favorites are the flor de las antillas toro and belicoso (went through a box of the toros way too quickly), or the el centurion, which is a VERY underrated offering in the lineup, also would recommend toro or belicoso.