It really depends on your taste. Most every cigar I've had has been enjoyable out of the box. Do they get better after a few years? Aging potential largely depends on the cigar, but typically, yes. I enjoy the more subtle and silky smooth notes from a really well aged cigar.
Cigar smoking is really a long term hobby. Buy some to smoke and some to put away. In a year's time compare the two and see what you like. But by all means, if you like a certain cigar fresh then smoke them fresh. I really like the Padrón 1926 line as they have a bit of that smooth aged taste right away. You can exhale them through your nose all day without feeling like your nose hair has begun to smolder.