Pay particular attention to the yards, driveways, and exteriors for clues.

Remember your costs will be more for an STR, you'll be paying for a lot of things you wouldn't with an LTR - higher STR insurance, all utilities including internet, supplies like toilet paper, paper towels, dishwasher detergent etc, upkeep on furniture and linens if damaged, yard maintenance and grass cutting/snow removal, trash removal, etc.  

Whats a good solution for a back yard to be easy to handle in the summer like in the winter?

I own a home and built an ADU in the back yard 2 years ago and net $1000 per month positive cash flow.  

You’re either his friend with a very pathetic attempt of possibly salvaging what little of a reputation he will have left, or you are also part of the problem.

I recommend setting your expectation of the level of cleanliness, maintenance of the yard and grounds at a very high level to the tenants.  

This amounts to lost opportunity because if you had purchased RE, at the closing it can start producing return. 5) ADUs detract from the existing structure whether this is privacy, a garage, or just yard space. 6) this is related to number 1, but there are many more buyers looking to purchase homes for their family than there are RE investors looking to purchase small unit count properties.

My rental property has sprinklers in the yard yet tenant will be responsible for paying for water.  

I've also seen two places near where I live listed for rent (signs on the front yard) by one PM. 

But there is hope... if you drive through the 4th ward area, you can clearly tell which properties are owned (single family homes with kept lawns and neatly decorated) and which properties are rentals (usually a broken window or two, falling apart porches, messy yards)... the closer to the single family-dense parts in the 4th ward, the better chance you have of getting a rental property that hasn't been laid to waste that you can purchase for a fairly cheap price.