The Regex always does its best to match. The only thing you are doing in this case would be slowing your parser down, by having it backtrack into the /o*?/ node. Once for every single 'o' in "tooooon". Whereas with normal matching, it would take as many 'o's, as it can, the first time through. Since the next element to match against is 'n', which won't be matched by 'o', there is little point in trying to use minimal matching. Actually, when the normal matching fails, it would take quite a while for it to fail. It has to backtrack through every 'o', until there is none left to backtrack through. In this case I would actually use maximal matching /to*+n/. The 'o' would take all it could, and never give any of it back. This would make it so that when it fails it fails quickly.
Minimal RE succeeding:
'toooooon' ~~ /to*?n/
 t  o  o  o  o  o  o  n       
{t}                           match [t]
[t]                           match [o] 0 times
[t]<n>                        fail to match [n] -> retry [o]
[t]{o}                        match [o] 1 times
[t][o]<n>                     fail to match [n] -> retry [o]
[t][o]{o}                     match [o] 2 times
[t][o][o]<n>                  fail to match [n] -> retry [o]
. . . .
[t][o][o][o][o]{o}            match [o] 5 times
[t][o][o][o][o][o]<n>         fail to match [n] -> retry [o]
[t][o][o][o][o][o]{o}         match [o] 6 times
[t][o][o][o][o][o][o]{n}      match [n]
Normal RE succeeding:
(NOTE: Similar for Maximal RE)
'toooooon' ~~ /to*n/
 t  o  o  o  o  o  o  n       
{t}                           match [t]
[t]{o}{o}{o}{o}{o}{o}         match [o] 6 times
[t][o][o][o][o][o][o]{n}      match [n]
Failure of Minimal RE:
'toooooo' ~~ /to*?n/
 t  o  o  o  o  o  o
. . . .
. . . .
[t][o][o][o][o]{o}            match [o] 5 times
[t][o][o][o][o][o]<n>         fail to match [n] -> retry [o]
[t][o][o][o][o][o]{o}         match [o] 6 times
[t][o][o][o][o][o][o]<n>      fail to match [n] -> retry [o]
[t][o][o][o][o][o][o]<o>      fail to match [o] 7 times -> match failed
Failure of Normal RE:
'toooooo' ~~ /to*n/
 t  o  o  o  o  o  o       
{t}                           match [t]
[t]{o}{o}{o}{o}{o}{o}         match [o] 6 times
[t][o][o][o][o][o][o]<n>      fail to match [n] -> retry [o]
[t][o][o][o][o][o]            match [o] 5 times
[t][o][o][o][o][o]<n>         fail to match [n] -> retry [o]
. . . .
[t][o]                        match [o] 1 times
[t][o]<o>                     fail to match [n] -> retry [o]
[t]                           match [o] 0 times
[t]<n>                        fail to match [n] -> match failed
Failure of Maximal RE:
'toooooo' ~~ /to*+n/
 t  o  o  o  o  o  o
{t}                           match [t]
[t]{o}{o}{o}{o}{o}{o}         match [o] 6 times
[t][o][o][o][o][o][o]<n>      fail to match [n] -> match failed