Richard,
There is a lot of different elements to this and though I do not like
the practice, I will answer in-line for clarity.

Richard wrote:
I want to tell you a short story to give you background, then ask for
your advice about entering a race series.

I have rearranged my schedule so that I can sail next June-October in
a Wednesday night "Beer-Can" race series. I'll be sailing a Catalina
250 or 27 in the "Cruiser" class. (No spinnakers)
Which? And is it your boat?

I would like to implement a plan that does the following:

1. Put together a crew. (Or if I can put together two crews, we can
practice/race together to keep an edge on and learn together until
June.)
This will be the hard part. Find people that seriously want to be crew
and then impress on them that every member of the crew(team) has to show
up (at least) or there is no crew.

2. Begin practicing and learning on Wednesdays until June.
Good Idea

3. Compete and do well in the series.
You hope.... People tend to think that JAM/JOG (jib and main/ jib or
genny) is easier racing than the spinnaker classes. I got news for
you.... If you come around here and expect that you will finish
mid-fleet the first season, you will not likely be disappointed.

My background/experience:
a. Completed beginner, intermediate and advanced U.S. Navy classes
(qualified to rent Cat 250's and Cat 27's.)
That's good
b. Crewed in a few races.
Good Start
c. 100+ hours local sailing experience.
There are 168 hours in a week.

I have several books on racing and rules. I understand the basics of
rules, but right now, lose most rules in the heat of the moment.
You better fix that before the first start. Learn and understand the
basics COLD Port/Stbd, Windward/Leeward and Room at the Mark - Then
study to learn what changes them.

I've ordered a bunch of sailing books.
I hope two are the Gladstone books.

I'm getting a feel for rigging and getting in a groove upwind, but
have no clue what I'm doing downwind. (If the strategy is anything but
head for the downwind mark, I'm not sure what course(s) to steer and
why.)
Join the club... This could well be the toughest part of JAM sailing.
What you do is completely boat and condition specific.
Hint - Until the wind is solid enough to hold you over hull speed
trimmed as wing and wing, you will probably want to tack down wind.
Dead down is usually slow. Spinnaker - JAM it doesn't matter.

I'm starting to build checklists for what to do at the dock, in
the hour before the race, etc. so I can get into a structure routine.
Things to do before you depart: Check the weather. Pack enough drinks
and snacks. Check the Weather. and Oh-yes Check the local weather.

Understanding what your local weather does, what the reports mean out on
your racing ground and how changes typically occur is second in
importance only to you tactics in these club (aka beer can) races.

So..... My questions...

How do you like my plan?
So Far - So good.
What is your advice on things to do, include or avoid?
Sail for as many seasons as you can in spite of the fact that you will
probably get your ass kicked for the entire first season. When you
start finishing in the middle of the fleet, get a set of good used
sails. When you are near third more than a few times in the season, go
out a get a completely new set of race quality sails (expect 4k$).

Important things to do. Keep your crew happy. Be sure that shouting to
be heard does not sound like shouting at the crew. You don't have to
buy all the beer, but shouldn't beat them up when you/they are learning.
Mistakes will happen (if there is no blood - it wasn't a big mistake).

Get your crew to communicate (use standard signals):
Ready About
Ready port
Ready stbd
Ready frwd
Hard A Lee ..... etc.

Learn the boat - expect this to take at least a season. It typically
takes someone that has been sailing forever most of a season to do any
good with a new boat that is very different than what he has been sailing.

What can I do when there are no other boats around to find out how I'm
doing?
Not much... This is why IACC teams have trial horses. If you have
really complete instruments (must have true wind speed and bearing) you
can still only know how you are doing against the boats VPP tables.

This is probably more answer than you wanted, but it really is about a
minimum for the questions asked.

I always advise anybody with interest to sail as crew for a couple or
more years before buying a boat to complete.

Don't know how? Go find the club that puts on the races. Have a seabag
packed with essentials (clothing, foul weather gear, sunscreen...) and
maybe a 6 of something and stand around the club. someone will need
crew (always). Maybe just rail meat, but you will get to meet the
people that you need to. When you talk to them, be clear about what you
know and what you don't - if they have to find out you don't know, you
may not get invited along again.

Everybody (else) had to start sometime. If you want to be dependable
crew, there is always a need.

Me - I must have started too, but it was soo long ago and I was so young
that I really don't remember. I've brought others in though.

Matt Colie
Lifelong Waterman, Licensed Mariner and Perpetual Sailor