I reached out to a local roofing contractor (Supreme Remodeling Inc.) and got a quote that was $15-25K for Asphalt Shingle and $25K and up for Tile for a 1,450 sq.ft SFH.

There were 2 gable roof additions added where shingles were installed that don't quite match the existing shingles3.  

How often do you have to do it and how long will it last.A few examples:  Replacing a small section of roof shingles is considered a repair and deducted that year.  

You may not always want that job and need to plan accordingly.15% is a common budget for maintenance.CAPEX budget can vary depending on the age of the systems inside and outside the buidling (does it have a parking lot, is the roof rubber membrane or asphalt shingle, do you have a boiler system or furnace, etc., etc.).Hope that helps - I'm sure there are others I didn't mention.

The may have grandfathered policies, but old wiring like fuse boxes, galvanized pipes, or even Tlock shingles may prevent you from getting insurance or paying for riders or having exclusions.   

Typical asphalt shingles...

So my fiance just purchased a property about a month ago, we knew the property needed some minor roof repairs such as flashing repair, however, once the repair guy got up there he discovered 4-6 layers of shingles on parts of the roof!

Also, make sure you know how many layers of shingle and/or cedar shake that is on the house. 

He said "older people, widows, folks who moved to Florida, call me back when you're old and sick".Well, we'e now old and sick.Recently, my wife recovered from pesticide poisoning, then had a bout of shingles, and we just happen to have a vacancy.

A "new roof" is great and will last 20+ years but there are plenty of people that just take shortcuts and put a new layer of asphalt shingles on top of the old ones to save time and money.