You and I are in very similar situations, although I live down here in FL year round (as a side note, I grew up in Crystal Beach, Ont, down near Fort Erie).
Wife and I are going back and forth on what type of boat to get: cruiser or trawler.
We both have committed to each other that we will do 2-3 years liveaboard, then after that time, decide whether to go further with this dream or not. She is retired, I've got a couple more years to go.
We both want to spend the first year in FL waters getting used to the boat - whatever boat it is. After that we want to take a crack at some time between FL and The Bahamas, then would like to take a run down to the US Virgin Islands and possibly points further south. Simple, right? Well.....
She's a retired interior designer, so she's loving the sexy look of the Cruisers Yachts Cantius 48. It is a great looking boat, and something that we could easily live on - in a marina somewhere in FL and The Bahamas. I don't think for a minute that it would be a comfortable ride down the Thorny Path or across the Mona Passage.
My choice would be a DeFever 49 with paravanes. Lots of comfort, built to outlast either one of us, extremely comfortable, fantastic engine room, lots of fuel capacity, GREAT fuel consumption (especially compared to the Cantius 48), but in her eyes it's about as sexy as Elmer Fudd.
So the debate continues. In the end, it's going to come down to "Honey, where do you want to go with the boat?". This will ultimately tilt the scale one way or the other. I'm easy; I'm tired of the rat race and you could put me on a Cuban raft and I'd be happy.
So as others have said, Welcome! and enjoy the search engine.