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My Carpe Diem Racing team was like this. When I managed/had a shop it was the shop team. After the shop I kept it alive using my own money.
I think I spent $4-5k a year on kits. I know one year I did about $8k, maybe $10k. I collected wholesale kit cost from the members, who were friends who wanted to race flying the CDR name, or just wanted to ride in the kit. I had no other sponsorship, gave nothing, received nothing. I think some years I was $5k in the hole on the club, but that was my hobby and it was okay with me. I didn't really have a business to write off, just race promotion (but that was the reason for the club, etc etc etc).
USAC membership was $175 or something, I forget. I haven't renewed this year. You get a race director license if you want to hold a race. You get some liability from USAC.
Your company's liability policy should cover you, but make sure with your agent. YOu don't want to get sued because someone gets hurt in your kit (rider/driver/whatever) and has to sue you to avoid bankruptcy (think medical bills). Suing can be totally not personal, just a need, but it happens.
Kits - you can get low volume kits. I know and like Verge. They have a low volume version of their kit. Don't expect too much of a discount from anyone until you hit bike shop quantities, like 25 of each piece. Some kit companies bundle like items, so shorts, bib shorts, are counted together, short sleeve jerseys and skinsuit tops are counted as another. Jackets usually separate. Things add up quickly.
You can sponsor a shop team/club, but you give up design control.
gotta go
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