Hey missa,
The best time to start asking is about the middle of the month...let me explain. If your event is in May and you know you will need XXXXX a letter sent in March or before April 10th assures that it will get into their hands in plenty of time and in time for their next budget meeting.
The challenge of being in a small town is the key here. I grew up in a town of 325 in Iowa and remember in high school (20 miles away) we did alot with the local insurance agents, lawyers, tax accountants, banks, market, feed grain elevators, actioneers, and yes even the meat locker would pitch in $25 when he had a good month! No one liked going to the funeral home but they were alwasy good about donating $100 and asked to have their card printed. You know, that was about all everyone asked. We'll help you if you thank us with our name printed in the newsletter etc.
And sometimes it's loading up the little ones and going from business to business and talking aobut what you are doing at the school and what you could use their help with.
I know live in Denver and it's not much different. Sometimes you find that shop owner that is happy to see a mom and kids with a request for a donation. As a matter of fact, our church's easter egg hunt was Saturday and to my surprise the credit union came with $150 worth of baskets and prizes for the kids to win! All I had asked for were or thought they would do was a couple things.
Before I forget, thank you. No really. Thank you for hanging in there and doing what you do best. You'll see, soon you'll be advising us and cheering us on!! Your kids are SO lucky!!