There are usually many visual indicators about a house that are small warning signs of structural issues, cracks in walls, cracks in the external foundation, sagging floors, the slope of the lot, water damage dry rot etc.

On other occasions, it is also possible that the prior owner appealed the former tax assessment to get a lower value.

And being on-call 24x7 isn't terribly appealing either!

Now with technology, there is so much info to at least show you visually how to do something. 

Maybe give him some visuals to show his boss if you haven't already.

I have always been interested and felt drawn to Real Estate as the appeal of owning a tangible piece of land has always been attractive to me.

The thought of getting money out of my primary residence now without the monthly paymets of a HELOC or refinace is appealing but not sure if it worth it in the long run. 

The Subject 2 deals strategy or technique seems very appealing to me.

Less buildings to worry about and less tenants to manage seemed appealing.

It's appealing because it is less than 100k, but do you see a good return on these over time?