I gave a lightning talk about this and heard that someone (falsely rumoured to be BooK) had managed 197, so I've pared this down to 184 by using map{} as suggested by Sergei Mozhaisky.

#!perl
$_=++$/x11 .<>;map{$i=$-[0];{map{1while
s/w((?<=W.{10})|(?<=W.)|(?=.{9}W|W))/W/s;/W((?<= .{10})|(?<= .)|(?=.{9
+} | ))/s||$i=~/./+print("$& $'\n")+last}"$`W$'"while/w/g}}"$`x$'"whil
+e/ /g
[download]

#!perl
$_= ++$ / x11 . <>;
map {
  $i = $-[0];
  {  
    map {
      1 while
        s/w((?<=W.{10})|(?<=W.)|(?=.{9}W|W))/W/s;
      /W((?<= .{10})|(?<= .)|(?=.{9} | ))/s ||
        $i=~/./ +
        print("$& $'\n") + 
        last
    } "$`W$'" while/w/g
  }
} "$`x$'" while/ /g
[download]

UPDATE

Having stolen more ideas from Timur Nozadze I am now at 175

#!perl -ln0
map{$i=$-[0]+11;{map{1while
s/w((?<=W.{10})|(?<=W.)|(?=.{9}W|W))/W/s;/W((?<= .{10})|(?<= .)|(?=.{9
+} | ))/s||$i=~/./+print("$& $'")+last}"$`W$'"while/w/g}}"$`x$'"while/
+ /g
[download]

#!perl -ln0
map {
  $i=$-[0]+11;
  { 
    map {
      1 while
        s/w((?<=W.{10})|(?<=W.)|(?=.{9}W|W))/W/s;
      /W((?<= .{10})|(?<= .)|(?=.{9} | ))/s ||
        $i=~/./ +
        print("$& $'") +
        last
    } "$`W$'" while/w/g
  }
} "$`x$'" while/ /g
[download]