About Us

Anna Amano

Anna was born and raised in San Diego and knows the city in and out. After working as a Legal Contract Administrator for years, Anna transitioned into property management in 2015, working at RJW Properties. Over the ten years at RJW Properties, Anna became very knowledgeable and experienced with all aspects of property management and the multi-family business. Anna was the office manager, and in charge of human resources, worker’s comp insurance, training onsite managers, and all legal issues. She supervised over twenty onsite managers and oversaw seven hundred units. Anna was heavily involved in recovering unpaid rent during Covid, by working with the city and county submitting emergency rental assistance applications for the tenants.  Anna has managed renovation projects on a very large scale, namely apartment buildings. It was there that Anna connected with Tom & John Cunningham and started managing all of their properties. Over the years, Anna worked with the Cunninghams on numerous projects and acquisitions. 

The Cunninghams and Anna decided to join forces and start their own property management company.  Anna’s has exceptional leadership and communication skills and a proven track record of improving occupancy rates and resident retention. She has extensive knowledge of federal regulations and landlord-tenant laws and is very resourceful with her legal background. 

Tom Cunningham

In 1982, after a career in the United States Navy, Tom joined World Savings and Loan as a loan officer making loans on single-family homes in San Diego County. In 1984 World Savings opened a commercial loan organization in many of the major cities of the United States and selected Tom Cunningham to originate major loans on apartment buildings and commercial properties in San Diego. Over the next eight years, Tom was among the top three producers of commercial loans in the United States.

In the early 1990s Tom was selected to lead a workout group formed to manage increasing number of foreclosures among world savings loans. This task involved the management, rehab, and sale of foreclose properties (mostly apartment buildings).  Tom was responsible for management of nearly 2000 apartment units throughout the United States.

In order to reduce the number of defaults in world savings portfolio, Tom instituted an option for selected apartment owners in default to use the rental income from their properties to rehab and re-rent any vacancies in their buildings until the properties were able to cash flow a new loan could be put on the property, which would be acceptable to both the lender and borrower. Tom’s experience in dealing with owners during his years at World Savings have proven to be invaluable. 

Tom acquired his own portfolio of real estate in San Diego and other locals. Tom is excited to be part of the La Playa Property Management team and be part of a dedicated group of individuals and make a difference in our community.