However, it sounds like you live close enough to your properties that perhaps this arrangement will workout.

It's always a great sense of accomplishment in a mental boost when you finish a workout.

Is this strategy really going to work out in your favor 100% of the time?

You can sometimes work out bulk rates with a company that will lower your costs but whenever you buy from a public auction, you are taking some risk because you are buying as is with no guarantee about the condition of the house or the title.

It is somewhat of a hack as there is also a building on the property that my wife will continue to work out of.

Sometimes you can work out no money down, but expect to pay higher rates.Owner financing isn't like getting a bank loan.

Working out more and Reading more of the suggested books from the famous 4........I want to get back to working out twice a day like I was.......felt so amazing after those workouts.....

What is there to “work out”?

With that much equity, you could definitely get some nice cash flow with appreciation to boot.I'm 55, work out hard, and eat well :)I recognized that my post wasn't a solid question, but I'm not necessarily looking for affirmation of my plan to sell. 

I just need to work out the timing.Looking forward to seeing where this one goes!