If the situation is that bad i.e. causing health issues then give the tenant an opportunity to break the lease and move.

Or is not having much in the way of assets and cash going to cause my portion to get dragged down?

Painting, cleaning up, etc - stuff that takes a lot of time but doesn't require specialized skills, and even if done poorly would not cause serious damage.

That may have caused small multis to look comparatively less attractive, when that is not necessarily the case.

Depending on your state, this may cause issues with what defines a tenant and what rights they will gain.

Also as far as Lethbridge goes rents have been very stagnant for a long time as there a lot of people here with just one rental or they are renting single rooms in they're personal property causing the market to be super competitive.

Too many installers do not size units properly which cause issues down the road.

This will cause lawsuits

There is a huge list of items that will cause a loan to be rejected - cracked window, uneven sidewalk, loose hand rails, even a small amount of peeling paint, etc.  

Well, Just like many other homes affected by the freeze in our area, every water pipe in our house burst, causing ten's of thousands of dollars in damages.