They always get contacted by investors looking for deals and a realtor can help the entire process be more trustworthy and smoother than some random person on FB.I myself am a realtor here in Houston with a buyers list I have developed over my last five years of being in the investment real estate space.

If you buy a random property, you are just hoping the tenant segment the property attracts is reliable.

In that scenario, the notice given to you during the middle of May served to terminate the tenancy at the end of June (not some random day in the middle of June).

People use STRs for small vacations/ parties/ random travel just as much as massively planned vacations. 

People don't want to visit random neighborhood of Nashville, TN (unless they are trying to stay next to family). 

Everyone's "should I" is personal to them and some random strangers don't understand the details.

Just some random thoughts as I read your post. 

The cement brick under the house appears to be layers, but not mortared.The pic that appears to be under the decking, the randomness of the 2x4 would be a question for me. 

So I didn't pick a random Midwest market and now I know Indy much more to a detailed level. 

Many other random ideas come up, but the general gist of all of it is to highlight whatever is a priority to HIM and provide him that value.