As I have put on several other threads, having moved 19 times both here and abroad, for what its worth, my suggestions are
1. when you have picked an area that you think will suit you, then look around and see if you can stay bed and breakfast or rent a flat . But the idea is to try it out in a couple of different times to see how you manage overall. so try staying in late january/early february, when it will be probably at its quietest and the weather might be quite rough and cold. Then try and do the same in the middle of the holiday season. That way you have spent some money trying it out, both busy and quiet and see how the traffic might affect you.
. If you do the B/B then if you like where you stay, the owners will probably be able to give you a lot of good ideas and tips both for good areas to look in and what are the best grocers etc etc, plus they will probably know all the clubs that are worth looking at.
2. Start now by ordering the local paper from one or two possible places. This is worth while as you get to see what goes on in the places you fancy, also reading the court news etc you can then see if there is a particular road or area which would not suit you and can make a note of that when you come to look at properties .
So it is sort of a little project. You might each make a list of pros and cons about moving, and decide whether you want to keep them private in the beginning or share them. When you have tried visiting places you can then come back to look at your list. Sometimes we can be thrilled about one particular aspect, to the extent of forgetting to look at more mundane things. So I would think it important to see what public transport there was and ease of getting to train station etc, should you end up unable to drive.
So I see this as a very practical idea, where you may find somewhere you absolutely love, or alternatively having tried somewhere you might decide to stay where you are but plan to visit to resorts for a bit longer at a time, whilst still keeping all your friends and contacts where you are. Whichever you find suits you it will definitely be cheaper and less heartache than actually moving and regretting it, I think. Good luck and hope you find the answer that suits you