My suggest simple rule would sqeeze it.  With n = 50 and k = 75,

if len(s) > n*k or s.count('\n') > n: squeeze(s)

would squeeze at 3750.  With k = 50, as 2500.

I am not sure yet what to do about wrapping.  For development, a count of actual lines might be more helpful than a variable number of wrapped lines.