Parking is always a hassle in Key West and for people who need access to their property parking can also gum things up. You can sense the exhaustion and irritation of the person who put up all these dire warnings:
Private parking lots help get cars off the streets but as you can ell there is no great compulsion to make the experience pleasant or even tidy:
Fifteen dollars to park in a mud hole might seem steep but consider how much a ticket will cost in a town where an hour on the meter is four dollars!
These lots fill up in winter. If you can find a place to park on the streets during your vacation you would be wise to park the car and forget it. Except that a vehicle left in the same spot for 72 hours is subject to getting a tow notice. Parking woes are so intense in town everyone seems to manage to get pissed off at everyone over parking.
Or ride a bike as the old timers will tell you with a sniff of disapproval. They don't hold with new fangled inventions like internal combustion or traveling out of town..;