The books should arrive ahead of time so you can review and prepare for the "ground school" (two classes that take place on Wednesday afternoons before the weekends on the water). If you have any questions, please contact Training Commodore at trainingcommodore@pentagonsailing.org

I am going to let someone more knowledgeable comment on when and how sail hours would count toward 80-hour requirement for 104.

Finally, are you taking 104/114 with Annapolis Naval Sailing Association - Home (ansa.org)? They have a combined class...

Hi Robert, the ASA 80 hour number is a recommendation, not an exact prerequisite.  What really counts is getting enough experience to ensure that you have your ASA101/103 sailing skills and knowledge down.  The amount of time this takes will depend on you.  But no matter what, more experience is usually going to put you in a better spot come time to upgrade, so you should definitely get out there.   The 104 class is designed to build on and advance the 101/103 skills (e.g., on sail trim/handling, anchoring, docking, nav/weather, etc).  Lots of the 104 class also focuses on (bigger) boat systems (diesel engines, heads, galley) that you will need to understand for chartering, so getting out on some of the PSC Bay sails will also help prepare you for that.