I keep telling myself that I'll keep this thing forever and it'll be my retirement.

I planned to retire off of STRs...had it all mapped out.

If you're already worrying about retiring before you've ever joined the workforce, you need to expand your horizons and consider work that is both meaningful and financially rewarding.

Far too many I have seen go many years with no retirement and then try to play catch up. 

Goal is extra cash flow in retirement for financial freedom.Dilemma: the cash flow from the property right now is roughly $1300 per month.  

Trying to find a creative way to partner with the owner, owner is retiring and won’t be able to hold it.

Provides “proof” of funds but the account is a corporate retirement plan that the buyer can not access without quitting his job or paying huge taxes, penalties and fees 6.

I think you need to start by figuring out what you’re near term goals are - are you wanting to generate enough cash flow to offset W2 income, are you simply wanting to supplement your retirement, are you looking for significant tax advantages etc.

I am 59 years old and i am getting close to retiring, so i need some other forms income. 

Despite being under the age of 59.5, which is the qualified retirement age, you can distribute the $25,000 because it is after-tax Roth contributions.