It is a basic question with many variables and posting here already yielded insightful helpful comments.

Too many variables between now and then but that's a safer time period to look at this differently. 

@Tyson E Keslar There are a lot of variables to consider in addition to the roles and responsibilities that you have outlined.

Long story short - you cant just take the current effective tax rate and apply it linearly to the new price - there are fixed and variable components of property taxes so it wont scale like that. 

Each option has its pros and cons that can impact your investment strategy and overall success.HELOC (Home Equity Line of Credit)Pros:Lower Interest Rates: HELOCs typically offer lower interest rates compared to hard money loans.Flexible Terms: You only pay interest on the amount you draw, providing flexibility in how much you borrow and when.Revolving Credit: As you pay down the principal, the available credit replenishes, allowing you to use it for multiple projects.Longer Repayment Periods: HELOCs often have longer repayment periods, which can make managing payments easier.Cons:Qualification Requirements: HELOCs require good credit and sufficient equity in your primary residence.Secured by Your Home: Your primary residence is collateral, which means a default could risk your home.Variable Interest Rates: HELOCs often have variable rates, which can increase over time.Hard Money LoanPros:Easier Qualification: Hard money lenders focus more on the property’s value and potential rather than your credit score.Speed of Funding: Hard money loans can be approved and funded quickly, which is beneficial in competitive markets.Flexible Use: These loans are designed for real estate investments, making them suitable for purchase and renovation costs.Cons:Higher Interest Rates: Hard money loans typically have higher interest rates and fees compared to HELOCs.Short-Term Loans: They usually come with short repayment terms (often 12-24 months), requiring a quick turnaround on your project.High Fees: Origination fees and other costs can add up, increasing your overall project expenses.For a BRRRR strategy, a HELOC might be the better option if you qualify and have sufficient equity in your primary residence.

There are many variables that affect the price of a roof replacement and I have seen a very wide range of prices.

BP has starkly contrasting advice when it comes to entity structuring - and for good reason because there are so many variables to consider. 

Taking an asset to liquidate is a significant hassle, loaded with additional expenses, time oh-so-mush time, and variables such as potential market movements, changes to condition etc. all these come together to very possibly devouring what your equity positions may be in full or more, leaving no real equity of securitization itself. 

Anything is possible with some variables.

@V.G JasonI think you're saying that for people who bought maybe at the tip top of what they could afford, if they take on more debt and/or variable rate debt adjusts and/or they lose a job and/or they get divorced, they'll be under a lot of financial strain / potentially unable to afford their mortgage.