They have no skin in the game after the house closes, the insurer does.I would highly suggest, with the condition you suggest the roof is in (5-8 years left on a shingle might as well be 0 with a preferred underwriter), that you look at Foremost, Berkshire Hathaway, and or USLI.  

A simple ranch roof DIY with a few buddies will cost you 2500 in shingles and $50 in beer :)  The copper roof we put on my frat house was $120k.  

I went to the county to see what it would take to get a permit for it, and fount out that the footers are not deep enough, the pitch of the roof is not right for shingles (and it had shingles), insulation was not sufficient, etc - I basically had to either tear it down, or rebuild it from the ground up.

The vinyl siding (yellow or cream) will be staying, the roof will be replaced with a new architectural shingle...Asking for color ideas for stucco and any other inexpensive exterior dress up ideas..

They said they had roof work done about 8 years ago but I see where it's leaked although the shingles look to be in pretty good shape.  

I found a brokerage firm that only charges me fees when I close a transaction, so remember that these brokerages are out there when it's time to "hang your shingle." 

The new roof that was advertised in the listing, and that I did not have inspected, turned out to be a new layer of shingles over 4 existing layers, including the original wooden shakes!  

For example, shingle roof in southern market area may have a shorter life expectancy than in a more northern climate.  

How about the roof on this house - what type of shingle was put on it 1-3 years ago?  

The property I was headed to look at and hopefully make an offer on has asbestos shingles.