Reference questions 1 and 5:
It might be better to address a few additional things. Are you going to be camping or are you staying in Everglades City (EGC)?
If you are staying in EGC and paddling the area you will find that you are in protected waters. EGC is protected by hundreds of islands and Passes. Ivey House also has livery service for Turner River, Halfway Creek, and other day and multi day trips. Google Everglades City.
If you want to put in at the Everglades National Park Station and camp, you have many decisions. You can stay in protected waters by going South to the Lopez River and stay at Lopez campsite (6 NM). Continuing South you will mostly find mangroves and there are only Chickees for campsites. All sites require reservations. You will also need to file a float plan with the Park.
You can go SW into the Gulf to Rabbit Key (7NM), or Pavilion Key (10NM). Pavilion has a beach. You can go West to Jewel Key or Cormer Key (4NM), have a beach. Indian Key (5NM) has a campsite and beach. Picnic and Tiger Key Have beaches are a campsite, and Camp LuLu Key is just a mile North of Tiger Key.
Use Google Earth, go to Everglades City and look around. You can see the beaches and routes very clearly.
In December generally only cold fronts will give you a wind problem. The winds and get to 30 mph. This generally only lasts a day or two. The remainder of the time we are affected by convection so the wind picks up in the afternoon to about 10-15 mph (maybe) or there may be little or no wind. The Gulf can get choppy but most of the islands can be reached by using the many small mangrove islands for protection. You will have no more than 100-200 yd. stretches or open shallow water. Temperatures are generally in the 70’s in December but, a cold front can drop the temp to the 40s. This is very rare. Recenlty is has been mostly in the high 70s to mid 80s…
2. Do we need a VHF radio or is a mobile phone enough (we paddle max. 20-30km from the ranger station).
I am safety oriented. I carry both. The cell is great and works in some areas. A VHF will help you to get a passing commercial boat if you have an emergency. Ask the Park Service about this.
3. Tides can be strong during the major moon phases but are manageable should not be more than 2-3 knots, in major channels. Stay along the edges and it should fine.
4. Any bugs around x-mas time?
Bugs, I hate bugs and depending on if we get a good frost and a harm December you will have bugs. The wind usually keeps them off of the beaches and a good repellent will quickly solve the bug problem. You will encounter “no-see-ums” nasty little things and mosquitoes mostly in the mangrove areas. I use a bug suit and biodegradable insect spray. I try not to put repellent on my skin. Check with the Park again for the bug situation. They are wonderful people.
6. Raccoons: I have not had any problem with Raccoons on the outer islands. If you are camping close to the mainland this may be a problem. I have had friends have their kayaks damaged and a plastic kayak scratched through. Hang any food in the mangroves to be safe. Cape Sable is notorious for raccoons.
7. Books: I can’t recommend a book for the area you are going. One is probably as good as the other. I would use Google Earth to look around and try Googling key words that are related to Everglades City and Chokoloskee, FL.
My favorite paddle in the park is 125 miles South. I do a 10 mile paddle putting in at Flamingo heading SW to Carl Ross Key and Sandy Key. Then either paddle to Cape Sable a 7 mile sugar white sandy beach or to NE to one of several mangrove islands. The trip is all open water with an typical depth of 2 feet. This trip can be affected by wind conditions and if you get the wrong wind and tide you really have a problem. Sandy Key is a bird sanctuary. The sunrises and sets are out of this world. Check out Places to paddle.
Another option is to put in at Goodland, FL, just a few miles west on US41. This will give you a number of options. Cape Romano has a several mile beach and can be accessed from the Gulf or from protected mangrove. There is a marina and hotel at the foot of the bridge. They charge $5.00 a day for parking. Check out the Naples/Goodland area on Goolge Earth. There are also some keys South of Goodland. You could arrange with Ivey House to put you in at Goodland and you can paddle South to the Park. This would probably be a strong 2 day trip or better as a three day two night trip.