Knowledge is power and worst case you'll discover it's not a career you want to do but have a better understanding for how it all fits together. 

Mistakes will be made, which can cost more time and money.

Recommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.

The biggest mistake is not truly understanding the exit strategy.

Having hundreds of hours managing a myriad of STRs you really get to learn and get a pulse on what makes a property successful, how to mistake proof a property, and what it takes to keep them performing optimally. 

They then informed me that I could either move forward with the management services, with a nominal discount of $110 for the error, or revert to the Lease Only Option and have the lease transferred to me without any security deposit, as none was collected by the property manager.This mistake has left me in a difficult position.

@Jason EspositoEven with your private Lender being family, is it anything you would do different from your previous deals, any mistakes that you learned, and during your deals besides having lenders that are family, is their anything that you can share that made you successful?

Learn on mistakes. 

@Martin Yip Toll So You are making a mistake treating your debt relationships as strictly transactions.

its difficult to understand that map, do you know the best and worst zip codes on the city?