On the other hand it has simplified my communication style on finances and basic home functioning and made me more tolerant of those who did not grow in the know on those topics.

Have to have a solid team in place to run things for you and good communication with them. 

Write clear, understandable leases with landlord provisions that you stick to, don't be an arrogant jerk flaunting your economic success, communicate often and humbly, reserve judgment when you can.

Again just me I got to thinking well there is not time in the day to do proper client communication and service.. people are going to be calling and want specifics so to me it just seemed like something that would get pretty unmanageable in the Case of a WATER LANDING.. 

They overpromise and underdeliver on scope of work, tenant placement, and management communication.

Fast Track should do a nice job for you....but do consider others as contractors vary greatly on quality, price, communication, and warranties. 

@Michael Greenberg A fellow host in St Augustine does what is probably the most cost-effective way to get repeat guests by simply collecting contact information from guests and with their permission, sends periodic communication and specials.

Ways to mitigate the risk is to continue strong communication with contractors with weekly status updates.

Strive for respectful, open, honest and clear communication.

They are very responsive, good communication.