Internet, at least in Havana, became a lot better in the last few years and a lot of people have now smart cellphones and are standing outside hotels and obviously know the password to piggyback the hotel network.
It is certainly true that some cars have replaced motors but some are original ( or as original as possible ) so I was in one that had a truck diesel engine and another one with the original 8 cylinder ( And a WORKING Air conditioning).
The USB is a great idea but the digital age outside the city centers and like in many countries economically challenged it is not so much computer as it its smartphones.
It is a bit like in Africa where these days the smartphone, and not the computer, that is becoming the carrier of all news.
Another tip for travelers.
Do visit all the colonial houses and museum of interest in any city. All museums are free but you will see immediately some of the people working there accompanying you, they will show and explain everything . After the trip please give them a tip.
Remember , none of these places will be air conditioned. Take plenty of breaks, drink lots of water, in May the temperature will be fierce already. At the same time it can rain and I've experienced flash flood with water knee high at our resort.
But there is so much to see!
Another great place to visit are the 3 ( I think) classical old Pharmacies of Havana. These places are great!
Calle Obispo is one of the most impressive places of Habana Vieja you will find there and around there several places indoors where people play.
But there are spontaneous groups basking out in the streets, I'd rather try those.
As for going around the island, provided that you have some maps and you are used to go on roads that are not maintained to the standard of an European country , and you bring some spares ( because there is no shop where you can buy anything in case you break down) you can really go anywhere.
I crossed the Island to go diving in the " Bay of pigs " and let's say that they roads were... interesting! But you will find the most hospitable people anywhere on hearth . If you are really looking for adventure you can use the railways, but it is most recommended that you use the paid services of a trusted person, they will provide you with all the logistic support that you may require or need.
I saw a trip reportage on Haiti ( I am planning to go on holiday to the Dominican republic ) on Belgian TV. Well, roads THERE are a real challenge.
As for handing out cash. Please do.People depend on this kind of things.
Seriously, do it discretely but do it when appropriate ( and not " just like that") People whom are in the tourist industry get all too complacent about this but other people who are not would be incredibly happy, most don't earn much ( for our standards but also for their standards).
By the way, many play " Tres" ( a string instrument) those need special strings , some even play the variation on the Tres invented by Compay Segundo the " Armonico"