Is a weeping head gasket a sign of imminent head gasket failure?

I recently bought a 2005 Subaru Outback 2.5I with a MA reconstructed title.  
It has power steering leak a little over 79000 miles and weeping head gasket.
I got it for $4450 with 2 warranties dealer 60 days or 2500 miles and a
C.A.R.S. warranty for 3 months or 4500 miles. Dealer seems to be paying
games about his warranty. He wants me to wait until June 26th. I believe he
thinks he wrote warranty for 30 days which is allowed by MA warranty law if
over 6years old and over 80,000 miles then he would not have to fix for
$100.My questions are actually 2. His mechanic says some bearing? Is failing
in rack and pinion.  I have not had car long enough to see if leak is severe. I
have not even put 200 miles on her yet. His other mechanic believes that
passenger side HG is weeping. Are these considered drivability issues?
Dealer  MA warranty ONLY has to cover drivability issues. C.A.R.S warranty
does not cover oil leaks only combustion,coolant issues which 2005 2.5 don't
have. They also can use crappy a ss USED PARTS and customer has to pay
for diagnosis and teardown so they might pay if they feel like it.  Car runs
excellent looks decent other than bumper cover,1 headlight,taillight looks
older than other,drivers seat has 4" rear on seam. Oil is overcooked by
thumbs width. I'm  changing oil this week. AT a little overkill but not much is
still red. I don't know about front and rear diffs. Coolant is nice and green as it
should be. Dealer states timing belt but water pump not  changed more b.s.
on his part. Is checking timing belt hard? Should I have transmission
flushed,cleaned serviced? Car does not seem to like 30MPH 25 ok 35ok
unless you use cruise control. Is this a concern or normal for Outbacks of this
era.