Thank you for your candid review, and please allow me to respond.
As most repeat visitors to the island, the history of how the St Kitts and Nevis was discovered is covered on any island tour that is being offered by either a Tour Operator or taxi cab driver. This question also gauges the level of interest in the guest. Some guests have no real interest in the history of the island, which is why a food tour appeals to them as this tour is about the local food and not a historical tour.
Our tour lasts approximately 3.5 to 4 hours in length, with plenty of time for discussions about the island as the tour unfolds. Being a North American and a cruiser, my experiences living on St Kitts is of interest to my guests as I can compare North American ways of doing something to how things are done on St Kitts.
We do walk through parts of Basseterre that may be undesirable for some of our guests. St Kitts, like many other Caribbean countries does have a garbage problem and walking along Bay Rd is a clear indication of that problem. Monday and Tuesday the garbage along Bay Rd is generally worse than the remainder of the week. The reason for this is the pop up food vendors selling their food on Friday and Saturday, not sufficient number of waste receptacles, so garbage is thrown on the streets, ghauts, and gutters. Large amounts of garbage is also on the street from the local fruit/ vegetable vendors from the market and the stalls. The garbage will be picked up later that day or the next. Having walked this part of Bay Rd almost everyday has allowed me to come up with this conclusion.
In April, a 2 day island clean up collected close to 1300 bags of garbage in only 6 spots with Port Zante and Irish Town part of the 6 spots. Please click on the link for more information on the clean up. http://m.sknvibes.com/news/newsdetails.cfm/96028 As one of the volunteers that came out for the clean up, I do take the time to acknowledge the on going efforts that are being made to clean the island.
In regards to you point about the homes in Irish Town dating back to the 17th century please refer to the following links as this will give you the history of Basseterre https://en.wikipedia.org/wiki/Basseterre
Having been on 5 island tours in 7 months with 4 different tour guides, the term 'trash house' is a home that has been built with recycled materials, usually sheet metal. A Tour of the island, especially in Challengers near Bloody Point, you will find many homes are still standing to this day with this type of construction. Homes dating back to the 1700/ 1800's can also be found in residential area like Monkey Hill and New Road among other neighbourhoods.
In regards to St Georges Anglican Church, I'm not sure where you heard the word 'bombing' as that word has never been used in my tours. In actuality, your friend is incorrect in stating that the earthquake destroyed the church the second time. An earthquake damaged the church in 1842, but it was the hurricane in 1843 that destroyed the church the second time. Please refer to the following links.
Regards to our hiking tour and the level of fitness of a Kittitan, to this date, we are still looking for someone to conduct our hikes, we (2 others and I) have reached out to fellow colleagues, posted on Facebook, have put out feelers to our friends, but yet we have had no interest. I have also interviewed 5 local residents to have more local guides do the food tour but have been told repeatedly the walk is too much for them to do. Our tour is approximately 8800 steps tracked by our FitBit guests or just over 4.5 miles. As I can not speak for all Kittitians, I can only go off of my experiences and interactions thus far. An interesting article to read http://www.medicaldaily.com/16-countries-more-obese-america-are-mostly-islands-explaining-obesity-rates-country-362352#.VqOqW0HZM3M.facebook
As stated on my tour, tourism is fairly new to St Kitts. As the sugar production ended in 2005, the focus was then shifted to tourism. Tourism is now being taught in school as it is now part of the curriculum. Tourism has become a high priority for the government, and increasing the levels of customer service to all residents on the island, not just in the tourist arras. With the 4 new hotel builds and the 2nd pier planned, St Kitts is an upcoming tourism hotspot and a heavy emphasis on customer service.
The comments on schooling and post secondary education, as I do not have first hand knowledge of this, my comments came from having conversations with guests and ironically enough Rosie and Leah from the Gallery Cafe as they are a wealth of information and always great on converse with our guests over desserts. It was actually their son/ brother that was one only Kit titian accepted that year at Ross. The universities on the island are a for profit international universities, so yes Kittitians can apply and pay the full tuition. There is also a vocational/technical college on the island where Kittitians can also further their education. As for having to go off the island for Kittitians to further their education that is also an option for them. My friends that I have made while on the islands, had to send their children to either the States, Canada or abroad to further their education.
While I do not have the Kittitian life experiences of your driver Leo as I was not born and raised on the island, I have spent a lot of time researching, reading, asking many, many questions and taking tours learning as much as I can. As I stated in my opening paragraph my tour is about food, not a historical tour.
If someone asks me a question, they will get an honest answer, based on what I have experienced personally or information that I have retained while reading or in conversations with others.
In closing, may I suggest the next time you are on the island, have some conversations with some Ex Pats, this may enlighten you about how life is like for a non Kittitian and their point of views I can ensure you their experiences and opinions will differ from that of your driver Leo. I would also recommend spending exploring some in the non tourist areas such as Monkey Hill, Dieppe Bay, Lime Kiln, Buckleys to name a few towns.