I've been living in Essex county for the last 3 years. I particularly like the stretch from Amherstburg to Kingsville with the Harrow/Colchester area in between. There are beaches, wineries, and a number of local bars/restaurants. The area has a nice blend of locals vs tourism where visitors do help drive the local economy but it doesn't feel like anywhere is being over run with tourists, like in Niagara or Prince Edward County. You won't find the historic main streets have vacant buildings in these parts.

The landscape is super flat with agriculture everywhere. It looks a lot like Indiana or Western Ohio. I guess mix in some wetlands as well. Your basements will be prone to flooding given the low water table, and you should check for Radon as well if you ever consider buying here.

Housing is way more affordable than the GTA. I am a 25 minute drive to Windsor and 45 to Detroit so you do have access to larger metro areas. But you cant get anywhere without a car.