That beats that yard sign anytime.

The leak may be in your yard, but it's his/her responsibility.

Its starting to bother me, and worry about too much disruption for tenants. heck i would be annoyed..His landscaper gives me a padded quote for yard fall cleanup.

If it was a basement with no exit or windows than it's quite different than a basement with a door to back yard, windows, bedrooms/living area.  

I try to follow tax rules and regs absolutely to the letter, but I would find a way to keep my personal yard guy under the $600 limit if close.I heard of a guy recently that had gutters installed on their home, which has a rental attached.

The building needs a roof but it is salvageable.

I added a dishwasher upstairs that I bought off Kijiji for $100, removed some ugly hedges, general yard clean-up, painted the upstairs rooms and built a new vanity for the upstairs bathroom.

I am not sure what your intentions are, but I am a huge proponent of investing in your back yard. 

I've found local lumber yards pricing is usually on par or better than box stores, and a lot of times I can get it delivered which is a huge plus!

We are now dealing with unexpected/overlooked yard issues: A giant rotting tree that had to be removed; glass and garbage in the grass and ground covering; a dilapidated fence with carpenter ants; trees/weeds that have grown through chain link fencing; graffiti on a fence.