Upload & Sell: Off
It helps to know what incentives other T&I companies in your area are offering before you submit a bid. I know other areas of the country, kickbacks as high as 50% exist. That blows my mind, but still, it's incredibly beneficial to know what the league has been getting prior to your bid.
I assume you're covered with good liability insurance. You have absolutely no business whatsoever submitting a bid without proof of insurance.
Make sure your proposal clearly spells out what is required of you - specifically. It should also spell out what is required of the league. Are you scheduling the teams for photographs or is the league? Do you require anyone from the league to be on-hand on picture day? Are you distributing the finished packages yourself? If so, are you giving them to parents on-site? To team moms on-site? Are you just giving everything to the board to have them distribute? Are you mailing them?
Is action work part of the proposal? If so, does your proposal ensure no other photographers or companies sell their work at the park? If so, whose job is it to police that type of thing?
Timeframes should be included in the proposal. How long after pictures are taken will they be distributed? How long after pictures are taken will you be delivering your incentive(s) to the league?
Does your proposal also include freebies for coaches? If so, what are they?
Does your proposal include sponsor plaques? If so, how many per team? What size? Custom engraved or generic 'thanks for being a sponsor' types? When will those be delivered?
Are you offering multi-year contracts? If so, 2 years? 3? Are there added incentives for the league if they sign for more than a single year? What are they?