I did my first organized event last year.
I did not do a poker run because of the amount of people needed to help. With just a couple of people we ran a memorial ride from New Jersey to Maine with a "remembrance stop" on the George Washington Bridge (and we had traffic STOPPED if you can imagine that).
From the start of planning to ride day was about 37 days.
A member of my department designed the t-shirts, and arranged for printing. Shirts cost about $10 and we sold them for $20.
I did not order enough t-shirts and ran way short, but who knows how many you need.
I was able to put together a secondary order of shirts, and that was a big help.
Expenses involved included the shirts, coffee and donuts for registration day, drinks and snacks for the 300 mile ride (several cages involved), plaques for family members, plaque for memorial garden, shrubs and plants for the memorial garden, I registered the domain name for 5 years
http://www.SalsRide.comIn the end I have about $600 left over for a memorial scholarship fund that should be in place by next week.
This was for a firefighter, so there was a lot of word of mouth.
We had about 50 bikes and 25 cars show up for the ride from Edison, NJ to the GWB and 7 bikes and 5 cars (one PU and trailer) continued all the way to Maine.
Right now, besides working on the scholarship, which we hope to make a confining fund, I am considering starting a LLC and applying for tax exemption status.
For 2008 we will do a local ride and I am picking the date based on convenience, not what else is running that day. On any given day during the summer in New Jersey there are probably several dozen events running.
We are picking the3rd weekend in June (rain date 4th weekend) as we figured more people would be available due to vacations not kicking in yet.
Oh and the biggest thing, we are doing this with a police escort, they are the best rides.
And we had an Assumption Of Risk" form to fill out and sign for all participants.
Hope this helps