This property will be a buy-and-hold which begs the question of whether I go with a bit more expensive metal roof or asphalt shingles.

Asbestos Shingles, Asbestos pipe insulation in the basement, Extremely steep staircases, etc.

It has a tile roof that was put on top of an old shingle roof. 

A rough summary of the letter is below.Annual water expense:                                  $2500Annual lawn expense:                                    $800Total reimbursable expenses:                        $3300Less December check for reimbursables: - $1500Total reimbursables due:                                        $1800Cost to remove sat. dish and repair roof/shingles: $275Professional cleaning / trash removal:         $600Total amount owed by tenants:                      $2675Balance of $4000 dep. to be returned to tenants: $1325Upon receipt of the letter, I reached out to the landlord asking to discuss the charges and state that we disagreed with some.

Missing about 7 shingles.

Pete, insurance isnt much more than a block, as long as the roof has reinforced roof shingles.

Will need some roof decking replaced, and new asphalt shingles. 

My then boyfriend, now hubby, is a contractor and together we remodeled the place doing everything ourselves except electric, plumbing and the flat roofs (yes, we shingled the pitched parts.)

My skill level is limited to upgrading an existing space with new paint, fixtures, flooring, and lighting; this includes exterior painting, roof shingle upgrades, and deck building. 

The home itself is a 3/1, 815 SF and it has a simple, low pitched shingle roof.