Seth, that is one of our concerns.

or should I work with the tenants and do land contracts to sell them the properties at a higher interest rate and higher asking price because I am sure none of them have enough for a decent down payment and also I am concerned that interest rates will increase and I will be stuck holding a low interest loan and my money could go somewhere else, also I do not want them back. 

Additional concerns: tax implications, risks, benefits, & any additional information especially involving paying the least amount taxes. 

My concern is that the timing would need to be correct for me personally- I would need to be prepared to take on another rental and have the time to find the property, etc. 

@Kevin R. this was extremely helpful, thank you!

Any other questions / concerns I should be taking into consideration with renting waterfront property to multiple families?

I’m getting concerned about the labor part.Am I being overly simplistic to think I could - between Home Depot laborers- thumbtack and people I’ve used for projects at my house - I could manage a small rehab ..?

I guarantee this discipline has invaded your daily life and you will be extremely successful.  

I am concerned that he may have been in the lumber yard and attempted to leave with more then her purchased.

My concern is when the bank pulls my deed what will happen when they see the original purchase price only 5 months prior?