No big, national, publicly traded banks will do this loan type.

Should I prioritize cash flow more and look into duplexes or other types of properties?

Looking for 'Investor due diligence' type of inspector. 

Most midwest markets offer this type of inventory.I am also beginning to talk to CPAs and attorneys, but I am not sure what questions I should have cleared at a minimum to confidently take the big step. - First, I recommend speaking with a lender to find out if you can purchase the property in the name of an LLC.

I’m not able to personally qualify for cash out refinances.I’m looking to sell my home located in Southwest Florida in a HOA community but want to remain in the home to lease- 3 years or more.Does anyone have experience with this type of program or have any suggestions for me on where to look to get this done.

What type of investing do you want to do?

An annuity is definitely a different level of risk exposure than this type of an alternative investment. 

If you are purchasing an investment property, and intend on using for investment purposes only, not personal use, it might be possible for you to rollover the TSP to a Self-Directed IRA and purchase the investment property through this type of structure.

It does not sound like you're in that type of market based on what you shared.

The type of properties I'm searching for are single family ranches and multi-family 2-4 units.