New roof options/ cost efficiency

[Sam Zawatsky]

I am needing to purchase a new roof for one of my rentals so I can get insurance, and have been given a couple of options;

1.) shingle tear off and replacement with Tamko architectural shingles- $6850

2.) the above option but with an upgrade to Certainteed landmark architectural shingles- $7600

3.) a metal roof over the existing old shingles.- $7900

Which would you pick? The roof currently leaks around the gutter/soffit area and has rotted some of the truss/ decking/soffit wood. I know metal roofs are supposed to be good, but putting it over the existing shingles kind of makes me feel uncomfortable. I wouldn't want old , loose shingles sandwiched under a metal roof for 50+years.