1. Where is a better "entry" level cruising ground? Weather?
Carribean as the weather is more predictable. It is still possible to anchor out in most places. Yes you need to be South for the summer but that is not a problem and the hurricane forecasting is very good. The med by reputation has either too much wind or not enough.
2. Is there a dramatic price difference in monthly expenses?
YES much of the med is now very expensive and is increasingly looking at the megayacht market. There are lots of places where you have to use a berth and the cost per night is $200 - $300 dollars. Fatty Goodlander has just had a big winge about this. Taking Meds to Sail the Med
3. Would one place be more suited for a 1 yr cruise vs a 2 yr cruise?
You could have a great 1 yr Caribbean Cruise by buying a boat in Trinidad and sailing it west to the East coast of the US or even to Canada through the Panama Canal. I do not know if I would want to do a 1 yr Caribbean cruise starting in Florida and following the the "Thorny Path" out. But people do. Or they go offshore from the Chesapeake to the BVI with some organised rally thing.
The med would be good for a 1 yr cruise but you need to think about what you are doing for the winter months.
4. More kids (11 - 14) in one area over the other?
Don't know, there are kids about in the Windward Leeward chain and they seem to get together in most anchorages. 4-5 teenagers just now in Prickly Bay Grenada
5. Easier to come and go into countries?
Easier for you as Canadiens to do the Caribbean. If you stay in an EEC country this rule applies
Do a search on Schengen visa rules as things are changing.
The general rule stipulates a maximum 90-day stay within a 180-day period beginning from the first day of entry. Provided a multiple-entry visa has been granted, one may leave and return a number of times within the 180-day period but the combined stay within the region must total no more than 90 days.
In the Caribbean you would usuallt find no problems as the coutries are so small you naturally move on before their long stay rules kick in.
6. Maybe I am discounting a good option on the Pacific? Not sure if we want to open water yet.
7. I will have to buy an offshore capable boat regardless of where we go, and being from Canada it means buying a boat in a foreign country no matter which way we go.
Over 200 boats for sale in Trinidad between 30 and 50 feet!
I suppose I seem to be selling the Caribbean hard to you but I have friends cruising in the Med and they are all complainig vociferously about skyrocketing costs and anchoring restrictions for example one of the good cruising grounds in Croatia is the group of outer islands called the Kornati. When I visited it in the late 80s it was free. Now it will cost you $45 PER DAY if you buy your ticket in advance and $65 a day in the park. Menorca has just more or less banned anchoring in one of its main harbours.
We were in Teuleda yesterday and were visited by a chap in a Port Police RIB, who told us we had to leave, as anchoring was only permitted in the Cala if there were no vacancies available in any of the marinas in Mahon OR if the weather was such that you needed to seek shelter. Whatever the cause, there was a 3 day maximum stay.
BUT no hurricanes in the med. I am sitting here down in Grenada and the Cape Verde hurricane factory is firing depressions across the tropical Atlantic in machine gun fashion. All have gone North so far but about every 25 years one comes down here for a visit.