I too have done the Wilderness water way. Winter is the time to do it but this is when every one else does it as well. Be prepared to share camp beach camp sites and the Chickees will be crowded.
Bugs will not be a issue in February but I would never leave the bug spray at home when venturing into the Glades. Really the only issue is the weather and critters, racoons will chew through dry bags to get to any scrap of food. Bring food lockers beacuse there usually is not a trees high enough to hang food.
Frequent cold fronts will kick up the wind and the chop. Days can be long if paddling in to the wind on a ebbing tide. But all in all its a lot of fun and one of the best places to wilderness kayak in the US.
ACA Level 4 Kayak Instructor
Wilderness Systems Tempest 170