My favorite cigar, and I've smoked lots of em, is the Romeo no.2.
Good size, not too strong.
H.Upman is also another brand I enjoy, they are not strong like some cubans (cohiba).
I would also add that unless you are really into cigars I would look for the most inexpensive cubans you can find as you may not notice much of a difference and some of them can be wildly expensive.
P.S. Dominican cigars are grown from Cuban tobacco seed and you won't have the US border problem.
Edit for SP
My two cents
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