Insurance for packages? There isnt any, not at $3-$5 per tag, it would cost more than you can believe if you can find someone to underwrite it. Health insurance? thats on you as well. Welcome to reality. Yes you can write off equipment on your taxes, to be honest, starting with zero experience if you make enough to even pay taxes in year one Id be impressed. Save 15% of your gross to start with after 10k.
You will need:
1 bike
1 messenger bag
1 cellphone
groundbills which look something like this:
http://home.columbus.com/pedex/gbill.bmp
they cost about $50 per 500 in 3 part carbonless
usual tools for bike
open a bank account under your business name
file for a trade name at the florida secretary of state, that protects you from someone doing business under the same name
you wont need a tax ID number unless you will have hourly employees, your SS# is fine
determine your rate schedule and delivery area and print up some rate guides and business cards
some companies use zip code to determine distance, others use block numbers
I use zip codes, base price for the downtown zip, add $2 per zip code outside that
I offer 1/2hr, 1 hr, and 2hr service plus basic mail delivery for $3 anywhere in my delivery area which is about 20 square miles
Currently I charge $6, $4.50, and $3 for those service times, in june of 2006 I will be adding $1 to all of them.Roundtrips are double and I charge $20/hr for court house time, first 10mins free.
go get some customers and have at it
thats about a basic and complete guide as I can give you, its a decent start anyway