There are no dumb questions in this game.
First, learn how to cast an unweighted fly. hook size 2 to 20.(That means leader changes)
Then add size/weight.
At some point (with the proper leader) you will start having difficulty casting the heavy stuff.
Switch your "casting" mode to a "lobbing" mode for the heavy stuff.
For the Chesapeake, you will find that a 2/0 Clouser will catch almost anything worth while,
and you will conclude that the "heavy stuff" just isn't worth the bother. IMHO
An intermediate sinking line is all I use, and that extra line weight covers a very broad range of fly weights.
Dick