There is also the soft heart aspect of this for me, where the buyer is a single mother with two children and this will be her first house. 

There is also the soft heart aspect of this for me, where the buyer is a single mother with two children and this will be her first house. 

.-  Family friendly and decent schools- Within 1 hour of a really good children's hospital and an even closer decent ER.- Within 1 hour of an airport- Low taxes!! 

When our children got older and began to scatter across the country, we decided to rent it out weekly as a vacation condo since we weren't using it as much.

You did not mention anything about having a spouse or any children and my answers assume you do not have any. 

Our overall goals are to have a bunch of free time to be able to travel, and also start building up wealth for our 4 children.

He is a widower and has his own two sons in college, so I wouldn't want to use his money for my children's college educationI have some unclear financial matters with this rental plan and need some advice.1.

He is no longer on the lease and the children are young.

My tenant is hyperactive guy who constantly needs a project.

My advice to my daughter and son-in-law as they did not want multi-family, either, and wanted to buy a home to live in,  not just investment property, was to buy something that needs some work, plan to fix it up within the 2-year tax-credit time period, sell and keep profits tax-free, then buy another one that needs work and repeat until children need a solid school district.