PLPC need a few years to really shine.$275.
Shorts are pretty good young and will get better with age.
I would not think in terms of "better", but in terms of larger.
If you are thinking Cohiba, $250.00 barely gets you started, AND, Cohiba needs years just like PLPC.
Currently the value cigar is the Juan Lopez #2, $200.00 good overall quality and in your price range.
The Upmann Connie 1 is always a good choice as are the Mag 46. around $180. - 210.00
I have had some yummy Hoyo Epi 1s recently if you like the milder side. $210.00
San Cristobal El Principe come in around $120. and never let me down, along with a Parti Short box
$125.-140. you are there.
A box of Monte 4 and a box of RyJ Mille Fleurs leaves room for a Por Larr Panatela........ almost.