Send all new tenants a New Tenant Guidebook that highlights key processes in our system.  

Here are a few items they highlighted - repaint concrete sidewalk which had been previously painted and now chipping and replace a cast iron plumbing stack, which is functioning PERFECTLY, only because it is STARTING to barnacle.

They are not Highlighting the Ad or making is stand out in any way.

Then below, highlight that portion of the lease agreement they signed that you shared at the bottom of your post.

Third, look at the property with a new set of eyes: What features will you highlight?

If it has one, I would highlight that as a feature in the ad too.

@Alfonso SimmonsBrandon Turner’s book, The Book on Investing in Real Estate with No (and Low) Money Down, highlights a lot of options that investors have.

I would say most points have been highlighted. 

You highlighted one of my main concerns with short sales Nathan, I'm glad my thought process wasn't too far off.

This is just a hunch but I think these older investors might not fully understand the impact of technology (as highlighted in Long Distance RE Investing) and how it has changed the game and made it possible to invest out of state.