MANDATORY TRAVEL MEDICAL INSURANCE

From what I understand, travel insurance isn't mandatory in most cases. Maybe if the person looks sickly they force them to have/buy travel medical insurance at the airport. But generally provincial Canadian health insurance is enough to prove that you aren't going down to take advantage of their free health care.

If you are a Canadian, Cuba accepts your provincial health card as your province is your first insurer, when you take out private insurance the company is your second insurer and claims the provincial portion - they just don't tell their customers. Your province covers the first $50 of eligible out-patient care per day and the first $100 of eligible in-patient care.

So just make sure you have your health card. Yes, I have claimed from my province and was paid - took a long time
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I learned all this when pursuing RBC Insurance. For many years I travelled abroad and took out insurance with RBC Insurance - never making a single claim and during which I paid them thousands of dollars, until I got heat stroke in Cuba and attended a Doctor. The treatment was excellent. I claimed the $78 from RBC Insurance submitting the original receipted account and the note from the CADECA showing the exchange rate. RBC Insurance short changed me by $13.78. I had a protracted battle with RBC Insurance demanding all responses in writing, so I have record! Eventually they coughed up the $13.78 saying that they had made a "mistake". I told them bluntly that they did not make a mistake, they took a decision and I have never insured with them since.
I use my health card when in Cuba.

Good to know, thanks MacDuff. I keep hearing from the travel agents that travel insurance is mandatory, I guess they really want to sell it.

I think there are some insurance companies that offers health insurance also, through your insurance at your job (if you have any); I was surprised to find out that the insurance I have at my job covers also the medical problems when I travel

Travel agents are understandably in business for the money. The commission on insurance sales are a nice addition on the bottom line.
I never use travel agents, but compare flight prices on the web. In Cuba if you want to stay in casa particulars, then just go to the site: cubaparticular.com   which shows a selection of casas in all the towns in Cuba. The person operating the system is Raul Fuentes and he is VERY helpful. If booking you receive confirmation by e-mail and you pay the owner of the casa directly when you go there. There is no charge by Cuba Particular! Travel in Cuba by Viazul.  Viazul.com
Hotels are easily booked on the web.
If considering a location or an hotel, get on to Trip Advisor and read the contributions made by those who have visited or stayed there. It is a useful tool. There is NO need to get an agency to arrange things for you in Cuba - unless you are happy to pay them for taking a small amount of work of your shoulders. Beware of "experts"! 
I know the tourism industry very well as at one time I was Executive Director of tourism for one of Canada's provinces and I also have experience of organising and leading groups on specialist study tours to various countries. I say that so that you understand that I have deep experience. 

Thanks MacDuff,
I was told by a friend to check out couchsurfing.org as well, people offer accommodation there too.
Do you have any recommendation as to locales? I do prefer the beach, but the main thing is the friendly and down to earth type people, I don't want to meet a lot of hustlers, which I imagine would be more of a problem around Havana and some resorts.

The three outstanding attractions are probably Habana Vieja (Old Havana), Trinidad de Cuba and Vinales. But for example Che Guevara enthusiasts most of whom are unaware of his role in the executions without trial of some 354 people at El Morro in Havana and of personally executing his first victim by pistol and then as a medical doctor examining the effect of the bullet upon the brain of his victim, want to visit Santa Clara to see the very interesting museum buillt around the site of the train derailment which was a key factor in Batista's decision to leave for the Dominican Republic and the way over the top memorial and mausoleum of a few acres, constructed by Fidel ttheoretically as a tribute to Che actually in pursuit of the policy of cult of the personality.I mention that because you should first define your interests. I for example like architecture, art, music, walkiing and culture. Others like political history - revolution etc,
My liking for Trinidad which has during the last couple of years become even more popular leading to some changes, is the architecture, proximity to both beach - the playa d'Ancon - and mountains - and the music available at night at the various trovas, the town has several interesting museums. Distances are a problem for example if going to the eastern tip of the island at Baracoa where Christopher Columbus landed in November 1492, by Viazul, it is sensible to travel from Havana to Trinidad. Then from Trinidad to Santiago (2nd city) which has the oldest house in the Americas built by Velequez in 1517 and in wonderful condition - it is kitty corner to the City Hall balcony from which Fidel gave his victory speech on January 2, 1959 (including saying: "I do not seek power and I will not accept it.") From Santiago the Viazul skirts the coast and then goes over the tortuous mountain road built in 1962 to Baracoa. If you like walking, Baracoa has a lot to offer including the Alexander Humboldt National Park.
But it is possible to fly from Havana to Baracoa on a Gaviota flight - and as all three Cuban airlines are owned by the military, the pilots are all military officers. The combined Viazul fares almost add up to the air fare.
Most folks who have visited Cuba will recommend their favourite resort - which is OK if you like the three B's of package tours - Beach, Booze, Buffet, but the only Cubans you meet that way are those providing services - maids, waiters, coach drivers, guides - all of whom are trying hard to get tips as a $1 tip equals one days pay! In Havana you may be pursued  by the Jinteras - young ladies seeking either to provide sexual services or to provide company to enable them to get a free meal and some excitement in their otherwise dreary lives. Also there are males offering to guide or show you to a casa for which they get a few dollars from owners - and which is added to your bill !
Vinales which lies about 90km west of Havana is interesting but inland, the beauty of the Vinales Valley stays in ones mind forever and there is nightly music in a trova just off the tiny square. If you go to the tourist/bus office opposite the square you can with little difficulty persuade a taxi driver to take you for the day to the Isla de Justia for the day for 50CUC. The beach there is my favourite in Cuba and the sole restaurant serves good food with sometimes live music. The road is terrible, but that isn't your problem.
If you are seeking company, the best I can suggest is the trovas - because there is often a 1 CUC admission which deters many of the jinteras.
Well, I've rattled on a bit, but I hope it gives you more feel for the reality of Cuba. The essence of the social life of Cubans is "la familia" and the soul of the country is is music.
I shall be back there at home very soon. in consequence my comments here will end until early May.

Forget Viazul buses and go with Astro buses at a fraction of the prices and go pretty much everywhere the Viazul do and you travel with Cubans and not tourists .. From Havana to Santiago De Cuba I paid 900 NP One way =4 cuc
Forget the myth their only for Cubans..Never been refused and Im white as a ghost so they know Im Yuma