In the 15 years since, he's gotten older, had several children, and now wants to start planning for their future so he creates a trust and transfers title to the property into it for estate planning purposes and to avoid probate like @David Dachtera said. 

The biggest challenge I run into is getting my customers approved for a construction loan.

If you are open to multifamily, there are several properties in old louisville that meet your 1% rule, but those 100+ year old buildings bring with them other challenges to keep in mind.  

They taught their children to go to college, get a degree, get tons of debt from that degree, get a good job, then die.

We are living in a home and neighborhood we love and are a year in to a school that we love and would be happy having 1-2 children at for the next 8 years.

Three adult children have taken control of it.

It's really easy to cover up shoddy work and it's really challenging to find ones that are done right.

The challenge I have with some of the people on this forum though is that they make very direct assumptions and give advice about specific people without ever attending that persons seminar, without ever discussing the program with the person directly or without even discussing the program from someone who has attended the seminar or bought the product.  

if so, what Challenges have you faced here and how did you overcome?

I will be interested to see what the veterans say but I think it will be challenging.