I never even thought of these issues, ice-capades!
Is there one time-of-year/season that's better to have the info come out for LEO or other Fleet purposes?
Not really. The government agencies have their own fiscal year, budgets, etc. and fleet acquisition timetables and there's really no one time-of-the-year. It also depends how good the purchasing agent is and whether they pay attention to the fleet ordering schedules and deadlines. It's not uncommon for them asking to place orders after the fleet ordering deadline.
We're just about to finish delivering nearly (70) 2017 Transit T-350 MR Vans that were drop shipped for $20,000+ worth of upfits for each vehicle. Due to the long fleet order lead times, shipping, upfit installation time, shipping to the dealership, etc. it been over 6 months since the first batch of Transits were ordered. They've been delivered at a rate of 3-6 per week. Municipal orders for Explorer Police Interceptors average about 6-8 per department, per year, and those orders come in at all times of the year depending on the usual fiscal year, budgets, fleet replacement needs, etc.