Appliances, cook top on outdoor kitchen, and kids using the pool and ripping shingles off to play Frisbee. 

Paint doesn't last much more than 5 years unless it's on cedar shingles then it may last longer, Behr is good paint. 

My shingles were installed that afternoon. 

You could 20 year shingles up there and you could be on your 15 year and they could last another 15 years with a little patching.

When you compare costs for a used 16x80 and add in the cost of locating it, moving it, rehabbing it, the used home often ends up costing more than a new one assuming you are looking for a late model vinyl and shingle home.The types of deals that existed in the early 2000s were a one-time phenomena that may not happen again anytime soon.

Just an update though - during home inspection we found settlement cracks located above garage door, several cupped shingles on the roof and some soil eroding near side grading.

For example, they mentioned wear on 10% of the shingles of the main house.

It is common knowledge in the building industry that Certainteed Shingle Co. has a nationwide class action lawsuit going on relating to the quality of their product.

Just bought another last week, a 94 16x80 3 bed 2bath shingled roof.  

We started getting work done on the exterior like roof, windows, exterior paint, new doors, railing for the stairs… Some things are coming in below budget, and some over budget like the roof needed all new wood under the shingles.