Annexation isn't as hard as some would think. You should see the battles for land in high growth areas of Central Florida where you have several cities in one county.
Here's a look at the city limits of municipalities in Pinellas County:
Broward County:
Last, my home county, Polk County:
Take a look at Winter Haven and Lake Wales. When I was a kid, these cities were square boxes that were 15 miles apart. A mall opened in 1996, halfway between them and they went on an annexation war to gobble up as much county land as possible where they thought new growth would take place. Now the cities are weirdly shaped because in some cases, land was annexed to "protect" certain areas of future growth from being annexed by a neighboring city. In Winter Haven's case, this strategy paid off when CSX/Sunrail deal resulted in an intermodal hub being built right off SR 60. Although the site is more accessible from Bartow and Lake Wales, it's actually in Winter Haven's city limits.
Lakeland has done the same thing, stretching out along the I-4 corridor where Florida Poly University and new warehouses like Amazon have popped up. Auburndale is now getting into the annexation game to get as much land around I-4 and the Polk Parkway (it believes it has a right too) before Lakeland gobbles it up.