Just finished up a term as a PTO president, had this debate from every angle. I tend to dislike the middle man-cateloge fund raisers because the money you raise is split with the vendor, and you are offering high priced goods with little value that most people would never buy otherwise, and it functions on guilt and imposition of your friends and family. That said, the reason that they even exist is that most orgnaizations can't make that much money in any other way (we are talking about the thousands, when you have hundreds of children participating) So, with a sports team, I would guess that you are not in that situation, so you can probably make a better impression, and just as much money, by avoiding these kinds of deals. What we were finding in this econemy was that our parents were more favorable toward event based fundraising and buying items that they were going to buy otherwise.
Find some local restaurants, see if they will sponsor a few "family nights" for you. They kick back a percentage of the bills to your orgnaization. You can then pass out the fliers to your family, neighbors, and friends, and encourage them to eat out at that particular night. Pizza is especially popular, and if you do this once per month it adds up. You are not really asking anyone to do anything that they would not do at some point anyway, and they get the regular benefit that they would if they just went out to dinner, they just do so on your behalf.
If your organization is 501c3, this will help with the sponsorships, if not, you can still seek them for advertisements also. Real estate agents are good sponsors. You can let them plant one of their signs at your home games with some balloons on it, with a computer printed banner (try microsoft publisher) taped on it that says "sponsor." Landscaping companies, roofing companies, and construction companies also have yard signs and are looking for ways to get their name out there.
Some car washes will offer a code for your organization, and you get a kick back, or will let you work the car wash for tips on a given day.
Walmart will let organizations sell candy at the doors for donations. Call the service desk and get some Friday, Saturday, Sunday dates.
A garage sale is another profitable way to make money. If you can use the soft ball practice field, you may be able to organize a community garage sale, where you have a small space, but you also sell space to the rest of the community to come sell as well. Sell a 15 by15 food space for 35 dollars (adds up) then you arrainge for the publicity, a salvation army truck to pick up the leftovers, your team has its own space, and your organization sells hot dogs, sodas, bake sale items, does face painting, puts out a duck pond and lets kids win small candy items, etc. Check with the city before you do this, you may need permits.
Just a few things working for us.
M.