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. 

So my tenants had to go (repeated late rent) and when I got 'home' to start cleaning/fixing etc I discovered a pile of branches in the back yard; the tenants had Butchered my beautiful Prairie Flame Crab Apple tree - as well as removed several branches from my sugar maple. 

The HOA went into the back yard (without permission) and found the following:-Blue tarp folded up in the back yard -A row boat that is rather small (we didn't know it was there but it's very small and not a big deal for us)-An item on the roof that looks like a small table that was blown up there (we agree with removing this)We agree with some of these items, but I'm particularly concerned with the trespassing and identification of items that are not within the control of the HOA.

A recent study found that 52 percent of home buyers relied on yard signs frequently or occasionally during their home search.