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I'm familiar with Bushwick too. Kind of a tough looking area. But just across the borough line in Queens, the Ridgewood section looks fairly nice. Lots of nice row houses like you see in Brooklyn and a healthy looking commercial strip along Fresh Pond Road.
I'm a big fan of upper Manhattan. I've lived in Washington Heights for over two years and really enjoyed it. Inwood is similar to Washington Heights. Also, Inwood has historically had a substantial Irish population. One nice thing about upper Manhattan is fast access to many of the places you want to be. You will probably be closer to the subway than you would be in Brooklyn or Queens. And the A train runs express (except late at night), getting you to midtown and beyond very quickly.
In your case, I don't recommend Williamsburg. The neighborhood does have cutting-edge art and music. The problem is that it's just not very socially accepting. If you don't fit a fairly narrow definition of what it means to be a hipster, people won't give you the time of day. The neighborhood also tends to be mostly people in their 20's. NYC has many fun, interesting neighborhoods where someone in their 60's can be accepted socially, but Williamsburg isn't one of them. I live here currently, but I've given up on using it for anything more than a commuter neighborhood and am looking forward to moving as soon as my lease runs out. Actually, it's not even that convenient for commuting to other areas. It can take me 45 minutes just to get to midtown Manhattan.
Bushwick is indeed rough. It's dangerous enough that I don't recommend it.
Ridgewood is also a nice area. One thing to consider is that you probably don't want to live in the areas within walking distance of the L train because they are somewhat rough. Thus, you're probably looking at relying on the M train. In many cases, you'll then have to transfer to the L train anyway.
I'm less familiar with the other Brooklyn neighborhoods you mention. It's important to understand that Brooklyn has a fundamentally different culture than Manhattan. Manhattan is much more individualistic. Venues and social groups tend to welcome a much wider range of people. Brooklyn is much more close-knit and insular. People keep to social groups which mostly include other people quite similar to themselves.
Windsor Terrace is very working class and probably slower than you are looking for. Its very quiet all day and night. You've be better off moving closer to the busier avenues. Park Slope will have more of the types of bars you are looking for along 5-6-7 Avenues.
Yes I get the impression that Windsor Terrace is working class and pretty quiet. That's part of the appeal for me. Plus it's adjacent to Park Slope so it should have some good places within walking distance. Should be a little less expensive than PS also.
I'm familiar with Bushwick too. Kind of a tough looking area. But just across the borough line in Queens, the Ridgewood section looks fairly nice. Lots of nice row houses like you see in Brooklyn and a healthy looking commercial strip along Fresh Pond Road.
I don't understand why people are so bent on continuing to sell him on hipster areas that have absolutely nothing of what he's looking for... Look up the original hipster definition of the 50s and 60s... Pay attention to what he writes and you'll realize areas like Park Slope, Astoria, and Williamsburg are not what he's looking for... To the OP, it seems like you have a pretty good idea of what you want already... The areas you've mentioned seem to be a good fit for you... I also think nei's suggestion about Downtown brooklyn is a good choice... Decent mixed area that in some parts almost has a late 90s early 2000s Fort Greene type of vibe...
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