Hey, frankly I have no logical explanation... my wife wanted to go and we go
Never been to Greece before... I am more of a Caribbean guy myself, so this will be different for sure...
Ha,Your wife sounds like a lucky lady.
"Advice" is fairly open ended. So random thoughts...
My disclaimer is that I love the Greek Islands. And usually go every year (but now the kids are a little older we are limiting to every other year so they get to experience other countries and cultures too.)
The Greek beaches will never compare to the Caribbean, in beauty and exoticness (think I've just invented a new word.) They are just as likely to be stony as sandy.
So if you want sand you will have to choose your destination.
Also the beaches can get busier than that in the Carribean, so if you want quieter beaches you will need to pick a quieter island with plenty of small coves.
Greece and the islands are defiantly a little more run down since the financial crises (like the bins mount up quite a bit now before being emptied), but the warm welcome and culture more than make up for this.
Crime, I think you would have to try really really hard to become a victim of crime on any Greek island! To the most part crime is none existent.
The sun and beach is not the main draw for me in Greece.(I get a bit bored of it.)
But its about spending all evening in a family run taverna chatting and getting to know the family over a few drinks. I like to read up on the Greek mythology for the island and visit places like the birth place of Zeus on Crete and any ancient ruins. On some islands like Rhodes there are ancient Greek ruins just lying around most corners. (google some images from Rhodes, you will be amazed)
I would definitely start learning Greek words, it goes a long way as an ice breaker.
Just a few words like thank you, your welcome, good morning/night, the more the better. I have been invited into Greek homes many times to eat, drink and watch football, which I'm sure would not have happened without an ice breaker of banter of a few Greek words.
For me the last thing I would do would do is stay as full or half board in a hotel, but instead I would stay as a bed and breakfast somewhere near to a few tavernas and enjoy your meals out.
I would avoid staying in a purely tourist built town (of which there are many) and stay somewhere where locals live and work too. There are lots of places that are deserted in the winter as the Greeks go back into the mountain villages to harvest the olives, these sort of places have no churches, no school and often no personality.
The other thing I would suggest is that if you have 2 weeks and you have come all the way from Canada, it may be worth splitting your stay to two islands.
P.s - If you like lamb you must try a kleftiko from a local taverna (it's a slow cooked lamb,where the vegetables are cooked with the lamb in its own juices, so the the veg just absorbs all the lamb juice. Its an old dish that used to be cooked in a fire dug on the beach). It's worth asking the locals which taverna does the best one. But do reserve it during the day as they take 4-5 hours to cook and often go really quickly in the evening.
Jason