The roofing industry is in a crazy place right now. Asphalt has historically dominated the industry in the north east. Formally asphalt shingles had enough petroleum in the shingle to help make the roof last for 25-30 years. However in recent times there has been less petroleum put into the shingles as years have gone on. So when a roofer says they don't make things like they used to....they were talking about the material content of their roof materials. Without the help of petroleum shingles are curling and cracking in 5-10 years instead of the 20-30 years that homeowners are pushing for.

1. Redo the roof every few years and eat the cost increases that are inevitable
2. Use Different Materials ie Metal, concrete, tile etc 
3. Make sure that there is no fine print in the warranty that comes with the roof
4. Make sure the plywood is in good condition underneath and there is proper underlayment 
5. Make sure when the roof is done that all roofing finish work is done properly IE rake edge, drip edge, ice and water paper to code, ridge vent, capping, chimney flashing, valley flashing etc