I know both NR and PW and both are very nice. NR has a greater range from lower class blacks to very wealthy whites (and blacks). I think PW is more homogeneous upper middle class and above whites.
NR has better access to land activities and the adjoining park lands are really nice, both Pehlam and Glen Island. I prefer the feel of the WHYS to a Brewers any day... call it charm, scale...whatever. Brewers is about as expensive as they come.
If you drive, the i95 is very close to WHYS as is a Home Despot and other big box store. Handy for shopping
. I think PW will be further off the LIE, but each are short train rides to the Manhattan. I prefer Westchester Cty to Nassau
Cty Long Island
Also within bicycle ranger
from WHYS are the Bronx Zoo and the amazing New York
Botanical Gardens. And there is great kyacking back in those waters. City Island is not protected so it can see swells. WHYS is really tucked in and safe. But the there is no cutesey town in NR. Bottom line for me, NR is a better location.
My preference is WHYS, but PW is a close second. As far as size.. I think 50' is not a problem if he has a slip. regardless of where you end up, I'll pop over.