The road network was surprisingly good and often very new. I think lots of EU money went into this remote corner of the world to prevent further emigration and to make this place worth living in for the local population. As there are quite a few car rental companies even on the smaller islands, renting a car is easy and straighforward. Cars are offered at the airports and ferry terminals, very convinient.
Failal, Pico and Sao Jorge, often called triangulo, are connected by several ferries per day. The ships are quite new and the terminals are shiny and comfortable. Baggage handling is like on airports. You buy your ticket, drop your luggage and pick it up again on a belt after arrival. Easy.
Between the more distant islands with no or irregular ferry connection several flights per day are offered by the local airline.
Accomodation is available, but during high season advance booking is essential. All kind of accomodation is offered, from hostels to 5* hotels, from self catering to alojamento rural. It is your choice.
Food is available in nearly all villages as you find (coffee) bars in even smaller villages. Fish, seafood and meat is tasty and often locally produced. It is again your choice.