I'm in nearly the same boat; only, we're trying to get back into biking. We were in Gainesville for several years while I was in undergrad and law school. During undergrad, we both rode with Team Florida (the club MTB team). Then, we raced with the gang from Razorback.
My wife kicked butt. She was fearless. Plus, she won most of her races; the best I did was 11th. Now, it's five years since we've been in the saddle, and we have a 19-month old daughter. But, we're gonna try.
We just got her Trek 8500 tuned up, and I just bought a shiny new Rocky Mountain Element 70. My daughter has a new Giro helmet and a sporty Trek GoBug for behind the bike. We're heading to Alafia (for the first time) tomorrow (if the weather cooperates). We'll scoot around the trailhead and some wide trails just to feel it out and see how my daughter does. We'll probably take turns babysitting at the trailhead while the other rides.
Ideally, we could pull my daughter on some double wide out to the technical stuff, and then take turns from there (probably possible at Santos -- not sure about Alafia).
If anyone with experience would care to offer advice, I'm all ears.