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Bologna quesitons... Would you live there? Where to stay?

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Hi out there,

My partner and I (in our 30s/40s) are planning a trip to small cities in Europe we might want to live in some day.

On our list so far:
* San Sebastian, Spain
* Aix-en-Provence, France
* Bologna, Italy

As you can probably deduce, we love food ;-)

I've started looking at VRBOs in Bologna and have started getting the impression that the city is a bit dark and dingy. Or perhaps it is just gray there a lot? Maybe there aren't a lot of trees? Maybe none of this is true...

If you have spent any significant amount of time in Bologna, is this somewhere you would consider living 3-4 months a year? Why or why not?

Are there other safe, beautiful, walking cities in Italy with great food you'd recommend?

Is there anywhere in the Italian lakes region that is large enough that one could regularly go out to restaurants and enjoy oneself for 3-4 months? (I am bewitched by photos of the beauty of this area, but it seems unviable for longer than a week or two.)

Finally, if Bologna is, indeed, a wonderful place -- can you recommend a hosted 2BR flat with wifi and breakfast anywhere? Or a small hotel that offers adjoining rooms?

I know this is a very particular set of questions. Big thank you to anyone who can provide any insight!

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