Put House on Market, Discovered Roof Leak, Now What?

[Robert Fisher]

My wife and I just bought a new personal home - one we can finally house hack!  We're going to sell our current home and use the equity to pay off my student loans (and because we wouldn't come close to even the 1% rule).  Here's our dilemma:

We found water damage on the ceiling as we were painting.  We call a roofer that is a friend of a friend, he comes the next day and "fixes it" at no charge.  We celebrate for about 4 hours until it rains and I got up to the attic to check on it - still leaking.  We get somebody else out to take a look and they recommend at least repair the last 2' of the roof and re-flashing the chimney - about $800.  I go ahead and get a quote on a full replacement - $6,180.  They both seem like a risk to me, but do we roll the dice and go high or low?

We're currently listed at $189,900.  If we do the $800 fix, I'm afraid we turn off buyers because it will be (and look like) a band aid on a roof that has 5-10 years left on it.  Even in our super hot market, I wouldn't surprise me if we had to accept $180,000 because we turned too many people off.  Am I thinking too worst case scenario?  Our agent has suggested biting the bullet, putting on the new roof and raise to list to $192,900.  This obviously handicapped our net to $186,000 before closing costs, even with a full price offer.  We have to spend $6,000 up front, but we still potentially come out ahead of the patch repair route.

We had originally thought to offer a $4,000 credit but are too afraid of the bank not loaning on the house if the roof is leaking.

What would you all do?  Which lesser of two evils is going to let us keep more of our equity in the end?