1) What are the duties of 'standing watch' and what are you watching for?
Depends on what watch you are on, and other factors such as conditions and locations, if your underway or not, the type boat your on and what the specific rules are of the boat. Far too many variations to cover in a Q&A post such as this. You need to do a Search Function for historical inputs on the subject of Standing watch.
2) When pulled in to a quiet inlet and anchored do you still need nighttime watch?
In most cased it is the same as above but typically one person is charged with anchor watch to assure you don't drag or your swing is poorly conceived at the time you anchored. This may or not be a awake on deck function. Most boats with GPS have anchor drag alarms that are in use after the swing and hold of anchor has been established for several hours after anchoring was accomplished. Again it depends on the conditions anticipated thru the night and the knowledge of the local anchorage shifts in winds/ currents.
3) Cost wise wouldn't you want to mostly anchor close to a town rather than use a marina?
I personally try to never use a marina and never anchor near a town. These are typically not places that are great anchorages. We do occasionally have to use them but prefer the more remote bays and coves we find while cruising and some are to be found in local cruising guide books.
4) If you anchor and take your dinghy in, where do you leave it and does it cost to leave it?
Many places you may visit will have dink docks specifically for those wanting to do business with the facility. Other locations will have community dink docks. These are generally at no charge. You should always secure you dink with chain / cable and a lock, not just a rope. Some marinas will provide free dink docks but some may have charges... you need to contact them by phone or radio prior to use.
5) on a swing keel boat, if you hit shallow reef does the keel move up?
Depends on you boat design. Those I have owned will move up but this should never be used as a given method of finding bottom as it can damage not only the keel but the mounting for the keel. Note that attempting to back up with a swing keel can be a very dangerous thing to attempt.
6) are you allowed nighttime campfires on the beaches of the smaller islands?
Obviously depends on the local laws of the land you are considering. No fixed rule exist, however if you follow the general rule of following the example of others or better asking a knowledgeable local source and if you take care and not endanger you will probably be OK.
7) what would be the minimum size boat you would use for Carib living?
No such thing exist. It all depends on the individuals involved. Some would say 50 feet, some 40 while others would say 10 or enough to set on. It also depends on the locations and conditions your going to be sailing and your qualifications in the expected and should be anticipated conditions you will face. Personally I have sailed in 32' to 58' mono hulls and find them all to be good depending on how many people are going to be aboard and the length of the trip. Boats get smaller with larger groups by the hour. A 58 footer can become a 12 footer in less than 3 days with ill selected crew. Since I single hand a lot and have smaller guest crews, I find my 36 footer to be fine for me
8) do you sleep on deck?
9) for extras what is the #1 must have item? solar? generator? microwave? elect fridge?
Depending on your personal preferences. Generally a boat size determines what you can fit into it. With most sail boats energy is the limiting factor for things like appliances, including a refrigerator/ freezer, radios, lights, nav equipment and lights. You would probably have to up grade your energy system if you want to keep things cold for a long time or operate something like a microwave. Solar or a specific generator will be necessary but understand that things like running a generator at night in an anchorage may make you less loved. I have installed solar panels and more energy efficient lights/ equipment and reduced energy needs in order to have my ice cubes at night
10) is Cuba safe?
No place is Safe... If your US you are not permitted to go to Cuba under most circumstances. If your not then you will find restrictions an port you can depart from. Cuba is not in the most frequented cruising destinations due to many other factors including currents and weather patters and its location in respect to the most frequent targets of the cruising population. It's hard to get to other Eastern locations from Cuba since you would be taking wind and current on the nose.
11) do you prefer a wheel or tiller for Carib cruising? Tiller gives more room in cockpit would be my thought.
Most cruising boats will have wheels, Tiller is just as difficult to get around as a wheel in most boats even in the up orientation. It is far less stressful on mid to longer runs to have a wheel. Most boats have wheels that can be simply removed while at anchor for longer durations.
12) is a dodger a necessity?
Depends on where your sailing, the weather and how dry you want to be. I find them to be far too hot and the cover over the hatch is not sufficient to warrant use. If I were going across the Atlantic I would not leave home with out one but in the Caribbean I find them much less desirable but it is an individual choice.
13) how long can you stay in the Bahamas as a visitor?
I don't know
14) is Turks a friendly place to stay?
I don't know
15) is a cat more expensive to stay at marinas?
Yes about twice as much due to width
16) does a cat have less rocking from the waves?
Depends on what you consider less rocking. I think they have about the same or more rocking than a Monohull at anchor and most other sea conditions. I can get really sea sick visiting a Cat at anchor but never on a monohull. They do not typically have as much tilt angle under sail if the seas are moderate. The most stable position for a Cat is up side down in the water.
Thats it for now. Thanks.[/QUOTE]
All are just person opinions and you will get different opinions particularly from the poor soles who are afflicted with multi-hull boats.