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As a tourist Whitby seems quainter, more bohemian than Scarborough. Most places have varying degrees of niceness though. Blackpool, for instance which is a right shit hole in places has some nice bits, my friend John is related to members of the De Beers diamond fortune people who live in Blackpool.
We've been to The Spice Mill Indian there which was pretty good.
There's one thing in Riccall that really freaks me out - the bloomin' water tower!
I've got a mate that lives in York centre, just off Bishopthorpe Road. His is terraced house and they can be had for reasonable money. The larger houses out in areas like Fulford and Dringhouses with gardens can be pricey.
York people seem quite down to earth and friendly. My sister lives in Harrogate, she fits in really well there - she's quite a snob!
The only thing wrong with York is, of course, the rivers. Looking at Rightmove, none of the ones on there allude even to the possibiity of flooding. Fortunately, we no where to look more or less.
And I know what you mean about the water tower................
Harrogate is a pain for traffic and has less going on.
Feel free to ask about specific areas, I know it well and have plenty of mates who live in York. As you said already the potential for flooding needs watching but otherwise it's a great place.
Pateley Bridge. In the Dales and again, wonderful place: http://www.pateley-bridge.com
Scarborough attracts vagrants. It's not as nice as it used to be in my opinion.
Stokesley attracts far too many travellers and a fair few chavs from Middlesbrough! but I agree it is lovely.
If I had to choose between Scarborough and York I'd choose Whitby by the way
If really pushed however, I'd probably choose York. It's a nice problem to have anyway. Good luck.
Give me a shout if you want to know anything specific about York, I've lived in a couple of different areas of the city and work in the city centre (although I now live in an outlying village).
York on the other hand is a different beast altogether and is often to referred to as the "graveyard of ambition", meaning people come here, fall in love with the city, then stay. I'm on of those people and I've spoken to many others who have done the same. Despite the slight increase in cost in living, it's better quality too. You're well connected; Leeds, Harrogate and Knaresborough all less than an hour a way. Plenty of places to go, things to do, sights to see, and there's generally a good vibe all the time. Not only that, it's a nice size for a city, everywhere being pretty much in walking distance.
Honestly, if you're aiming to move and York is an option, then pick York.