If he is looking to retire, the income stream will probably appeal to him PLUS there may be tax advantages to him too. 

Truly it was more of an appeal to the power of intention/positive thinking than anything else, but you make a great point!

Sits on almost an acre of landRoof: 15kGarage Door Repair/replacement :2.5kDrywall 5kFlooring: 5500HVAC: 8kBathroom reno 7.5kPaint 1kKitchen 7.5kCleaning out /Mis 2.5kCurb appeal- 1k5k contingency Comps from recently sold 155k 2 months ago not renovated smaller square footage I padded the renovation cost just to be safe and conservative rent in this area 1,200- 1400.

Also our current president's recent changes to tax law have disproportionately affected states with high property taxes, which makes owning property in lower-tax areas more appealing (property taxes in Jax are somewhat mid-range.)  

Lastly when is the last time you appeal your property taxes. 

That is a really good point @Jay Hinrichs - There is so much equity in the home I know I could do something great with it, and tax free makes it much more appealing. 

Here are some of my favorite tips:Curb Appeal.

These are things cash buyers and future home buyers (who will likely finance via banks) are wanting to see proof of even if the surrounding properties aren't presently at their aesthetic best.  

Network with experienced syndicators with a good track record and reputation of executing the kind of stratgey that appeals to you and your investors and offer to bring money to their deals. 

The more I think about house hacking again, the more it appeals to me.