I have lived here almost 20 years.. (am not yet retirement age).. moved from Brighton , and love it..
Schools are not the best apparently , (but you dont need them). No real problems with ferries ( although yes in bad weather they do stop)and you get cheaper travel for island residents . Have had no problems with medical provision , ( but yes, its an island and one small hospital ) dentists are a bit f a problem if you need an NHS one but there are plenty of private ones ..
We have had no problems with broadband..
Most companies deliver , and most of the couriers (I have occasionally found companies dont or want to charge extra but we've never had any real problem sourcing alternatives..) .
Local high street shops are not great ,( but look at any high street at the moment) ..We have all the supermarkets.. , .. Its easy to get to Portsmouth and Southampton for shopping on the fast cats and link to fast trains to London etc ..
there are Some truly fab restaurants here and local food , but can be busy in the summer.. A fairly good of arty and music scene- again depends on what you re into of course..
You get a lot of house for your money here, but island jobs if you needed one can be problematic ..
But yes its a different way of life.. if you like being outside, beaches , cycling , sailing , walking , etc etc you'll love it , if you prefer city life well then not ..
We live over in West Wight which is lovely but more rural. Depending on what you like, I'd recommend looking here, or around Cowes, or Ryde . (Personally I dont like Sandown or Shanklin areas which are more old style seaside .. )
Ventnor area is popular and keeps being mentioned in press as 'up and coming' but is difficult transport-wise and for things like summer sea fogs and difficult broadband and DAB signals..