Hey man, I tried to answer your questions back by PM but it said it was too long... so I'll just post it up here instead.
Honestly, I would just use good bagseed for your first season (think of it as a learning season) - unless money is no object or you have a way of getting feminized seeds cheap... feminized seeds are just too expensive for most people to use while learning.
On my first attempt growing outdoors I probably went through 20-30 seedlings (maybe more) before I started getting the hang of preventing everything from drought to flooding to animals to insects to people from destroying the plants. And even then a lot didn't make it to harvest thanks to a tropical storm.
It's one of those things where you just have to jump in and learn the hard way. But just concentrate on the basics at first: plants need food/nutrients in good soil, water, sun... and to be hidden. So before germinating anything jump on the outdoors section of the forum and read/ask about soil preparation, nutrients and feeding outdoors. Soil preparation and feeding is important - it's not as simple as just putting the seeds in the ground and waiting if you want a decent harvest... definitely have to research and plan what will work for you and your plants, get a shovel, buy your amendments and nutrients, and start preparing a grow site (covertly).
Speaking of grow sites - when picking a spot, safety and security is concern number one. Make sure it's off the beaten path and hidden well. Short of law enforcement - most people that stumble upon a pot plant will rip it or report it and waste all your work. Don't leave trails/tracks to it, don't leave trash around it... be like a ninja of the swamp and leave no trace.
Second concern is making sure the area isn't flood prone (like most of FL is), there is a clean water source near-by (but not too close), and the area gets direct sunlight for most of the day. Rain (almost like clock-work in the FL summertime) will naturally water your plants most of the time, but be prepared to head out to supplement if drought conditions come about. Otherwise, flooding from the frequent rains/tropical systems are usually a bigger threat than drought here. You won't need to water every day - that's too often even indoors. The plants will develop deep root structures in FL sand and gain access to the shallow water table here. So it's unlikely you'll need to water them much once they are mature, depending on your spot, drainage of you soil, and local weather. There's no hard and fast rule with how often to water unfortunately - too many variables. But my advice is just to watch the varied plants near your home - if they start drooping from a dry period, your plants at the grow site will likely need help as well.
Random other tidbits:
Get green chicken wire (or equivalent fencing) and use it to put around your plants (or entire grow site). Work it in to local vegetation to camouflage it from both the ground and air. This will deter smaller animals like rabbits and rats from munching. Buy/make deer deterrent and use it from day one at the site.
Insect repellent/killer - A small amount of dish soap diluted into water and sprayed onto the plant will tend to drown any present insects without harming the plant. There are also quite a few home-made repellent recipes you can find here in the outdoor forums. Generally, you'll only be able to use insecticides/sprays during the vegetative period. Once flowering begins, your options become limited unless you like buds with bad chemicals on them. Research Bacillus thuringiensis (BT), get some, and start using it before your plants start flowering... caterpillars will literally be waiting for buds to start forming so they can eat them. Kill them with BT before that happens.
Anyway, this is getting longer than I planned so will cut it short.
Just one more thing though - if your spot is near a lake or any body of water, people will be in the area at some point no matter how remote. So make sure to keep that in mind and be double sure you cover your tracks/trails/presence in the area well. Consider what everything would look like from a helicopter as well as from a hunters point of view on the ground and camouflage accordingly. Be safe!