I like the nickname [name_m]Ozzy[/name_m], but not the name [name_m]Oswald[/name_m]. I prefer [name_m]Oswin[/name_m].
[name_m]Radcliffe[/name_m] is cool, but I don’t really like the nn [name_m]Rad[/name_m].
I don’t like [name_m]Wolfgang[/name_m] (wolfie) or Hartford ([name_m]Hart[/name_m]) at all, personally. They just don’t fit my naming aesthetic.
[name_m]Benedict[/name_m] is becoming more usable, which I like. The nickname [name_m]Eddie[/name_m] works too, but might not be what you’re looking for. [name_m]Woodrow[/name_m] isn’t a favorite of mine.
Another nickname for [name_m]Benedict[/name_m] could be [name_m]Ned[/name_m], [name_m]Ed[/name_m] or [name_m]Eddie[/name_m] (my favorite is [name_m]Ned[/name_m])
My favorite name other than [name_m]Benedict[/name_m] is [name_m]Wolfgang[/name_m] though none of those names are really my style
I like [name_m]Wolfgang[/name_m] and [name_m]Oswald[/name_m] (though I prefer [name_m]Oswin[/name_m], too). [name_m]Benedict[/name_m] is also good. I’m a fan of [name_m]Ned[/name_m] - that might be my Australian taste, though. [name_m]Benno[/name_m] might be another option, or [name_u]Nick[/name_u]/[name_u]Nico[/name_u].
[name_m]Radcliffe[/name_m] and Hartford are nice - I’m not really into place names/surnames as first names unless they have a family connection, but if those two were in my family tree I’d be pretty tempted to use them as middles.
I prefer [name_m]Ozzy[/name_m], Wolfie and [name_m]Ben[/name_m]/[name_m]Ned[/name_m]/[name_m]Eddie[/name_m]/[name_u]Nico[/name_u] to [name_m]Rad[/name_m] or [name_m]Hart[/name_m], which seem a bit much. I like unexpected nns for more conventional names, but prefer more understated nns for unusual or unexpected full names. Of course, that’s just personal taste.
If you do want more nn options, I think Raf (my favourite)/[name_m]Raff[/name_m] or [name_u]Ricky[/name_u] work well for [name_m]Radcliffe[/name_m]. Another option is Riff (more like [name_m]Rad[/name_m] in style, but slightly less expected - if I met a [name_m]Radcliffe[/name_m] nicknamed [name_m]Rad[/name_m], part of me would probably wonder if the name was chosen for its cool nickname. If he were Riff, I’d guess he had a family name or a traditional name. I think that’s because I assume less obvious nicknames have developed over a long time). I also quite like Hartie/[name_m]Artie[/name_m] or [name_m]Harvey[/name_m] (Harfie?) or [name_u]Hartley[/name_u] for Hartford. And [name_m]Art[/name_m]'s an option if his personality doesn’t fit the name.
[name_m]Woodrow[/name_m]'s my least favourite, but it probably works better in the US than here. If you don’t like [name_m]Woody[/name_m], maybe Rowie, Drow, Woodsy or Wow/Wowie might work for you?