@Kyle PascualFirst of all I would get out of stock and sit in cash for the short term the Fed as you know just drop rates by 1/2 of a percent last week over the last 30 years anytime that has happened the economy has been in a recession within 6 months and the stock market has had a massive correction.

Asking in the correct forum will get a better response.Need a spreadsheet or form?

Asking in the correct forum will get a better response.Need a spreadsheet or form?

@Chris Seveney is also correct in saying "it depends."

I am planning to buy and maintain my property myself...

@Chris Seveney is correct though in this scenario your going to need cross collateral.

He simply wants to be 100% done.Given the above mentioned scenario, I am wondering what the best possible situation would be to make this happen, while possibly still maintaining the option to pull out equity for capital improvement projects with a bank. 

I think there's a lot one can do on their own to maintain it, but it does require diligent effort.

The STR deal could be the best option if I understand your situation correctly, except I would probably do this as a cash-out refi and just use the combination of booking history + AirDNA projected income to qualify (if not operated as a STR for a year).

What you’re describing, often called Residential Assisted Living (RAL), can definitely be a lucrative and rewarding strategy if done correctly.