The standard maintained by most lawncare companies is 42 cuts per year. At least once per week during rainy season (June 1 to November 30) and at most once every two weeks during dry season. I'm a community supervisor and our contract calls for 42 cuts a year.
$100 a month is too much in Kissimmee. You can easily find good companies who will do it for $75 or less.
Let me know when you're ready to look.
Weichert, Realtors - Hallmark Properties