Need Cuban recommendations.

[Lumpold]

I'm assuming you dad has bought cigars abroad before? Honestly, I can't really comment on the prices in South America or Uganda... but, I'd say:
PSD4 (A tubo would be more)
Partagas Short
Partagas 8-9-8 would be just over $10

RyJ Cedros de Luxe #1, #2 or #3
RyJ Tubos #1, #2 or #3

I've just had a Cedros de Luxe #2 I really enjoyed, but overall I prefer the Partagas lines!