Scootaloo will fly someday, once her pegasus magic becomes strong enough to compensate for her wings if they don't grow - just look at the huge white stallion with tiny wings (forgot his name) who somehow managed to enter Wonderbolt Academy. This clearly indicates that wingspan is not a critical factor in pegasi's flight capabilities. Normal-sized wings almost certainly help but under-sized ones do not ruin your chances.
Hey man, I'm working on a somewhat jazzy song and I thought this picture was perfect for the mood. Can I please use it as artwork? I promise to link here and give credit to you and the alike, but please, I just thought it would be funny and fitting!