Should I do the cashout refi and pay-off debt or use that cashout money for an investment property then utilize the profit/cash flow from that property to pay down the debt?

I guess a property can be financed with bridge debt or bank loan with unfavorable loan covenants leading to that scenario but that loan product is severely limited these days with unfavorable rates and terms.

My question to the group is do I sell my rental property that is paid off and end up paying capital gains + depreciation tax or would I refinance for let's say $280,000, pay off my primary residence and have $100,000 to either pay off debt or reinvest?

Don't forget, @Carlos Ptriawan, the long PUT option that you, the debtor of real estate, hold. 

I plan on eventually quitting my J.O.B. and fully getting into real estate investment consisting of long-term rental properties and mixing in some flips to help knock out other debt or to paydown mortgage balances.

You would not have additional debt or interest payments.

Also in terms of reward/risk, this is the era that's preferable to invest in :- investing in debt is way better (regardless it's real estate debt or any other activity debts)- investing in Gov. and corp. bonds and also TIPS- investing in CD.While avoiding investment in syndication, especially in office space area.Hotel syndication, however, seems way better post covid era.Investing in alternative debt acquisition is good way too to capture the commercial side that's falling due to cap rate issue.Everyday is a different day, some day it's good to purchase a regular house, and rental, but there are day where it's good to buy commodity, when too buy coal mining company, when  to buy tech stock and to buy bank stock.

This way the Hard money lender can now obtain the appraisal that they need to fund your loan, you can pay off the higher cost unsecured personal debt (or roll into into the next project for quicker expansion of your rehab business), and proceed with your project.Happy to chat more on this if this sounds of interest to you - feel free to shoot me a DM and we can chat there.

No student debt or car payments.If you are a hard money lender in the DFW area, I would love to network as well!

Rental property taxes and insurance is included as debt or as an offset to income?