Also hit up the yard sales in higher-end neighborhoods.

Thinking about Pittsburgh PA to begin with because it is my back yard.

I am basically end up ina  nice size apartment with yard for about $500 after top unit goes towards the mortgage. 

We had a neighbors tree fall on our yard and took out our fence and a retaining wall - we had to go through our insurance.

Of course, tough to build 50,000 units in one person's back yard, but there will be some people build granny flats, or garage apartments and you may see some office converted to residential. 

We rent single family homes, so we have a conversation about yard maintenance, snow removal etc - have you don't this before, do you have the tools etcI also bring up house cleaning questions, by telling them we had a tenant who did not own a vacuum cleaner, did not know how to run a dishwasher, had a mess in the basement etc - and then see how they respond.That is a non-offensive way to talk about house cleaning and you'd be surprised how different the responses are.

It's best to start in your own back yard if you can or somewhere where you can get to and home in a day of travel when you are starting out.

She deals with the property managers, the whole 9 yards.

2) If the lease that the tenant agreed to included them maintaining the front yard/ landscaping - is it reasonable to deduct a 1 time yard clean-up from their security deposit? 

Then people will be wishing we were just a yard-dart again because were gonna be a freakin comet hurdling back to level but things is now it takes that much more force to pull out of the dive.