I don't know if I've completely understood your problem, but some of the following might be useful. I've taken advantage of the extensions to Date provided in ActiveSupport:
d1 = Date.parse("20070617") # => Sun, 17 Jun 2007
d2 = Date.parse("20090529") #=> Fri, 29 May 2009
eom = d1.end_of_month #=> Sat, 30 Jun 2007
mth_ends = [eom] #=> [Sat, 30 Jun 2007]
while eom < d2
eom = eom.advance(:days => 1).end_of_month
mth_ends << eom
end
yrs = mth_ends.group_by{|me| me.year}
The final line uses another handy extension: Array#group_by, which does pretty much exactly what it promises.
d1.year.upto(d2.year) do |yr|
puts "#{yrs[yr].min}, #{yrs[yr].max}"
end
2007-06-30, 2007-12-31
2008-01-31, 2008-12-31
2009-01-31, 2009-05-31
I don't know if the start/end points are as desired, but you should be able to figure out what else you might need.
HTH