Post Dodd Frank sellers have continued the same bad practice of selling houses to occupants with financing at selling prices that are way high, can't be justified via any type of 3rd party valuation (appraisal, zestimate, tax value, even recent sales in the same area).   

Perhaps he runs negative cash flow while repaying the purchase loan or there is something I missed so my math didn't add up properly.  

A key risk is the due-on-sale clause, allowing the lender to demand full repayment, though enforcement varies.Keeping the property in an LLC provides liability protection, shielding personal assets from lawsuits.

Hard money lenders (HML) typically want to ensure you have the financial stability to handle the property and loan repayment, so proof of liquidity is a common requirement.

I suppose they would be able to help me figure it out but I’m still trying to determine what is the best way to fund something like this and would it be better to sell off the entire purchase once split into separate parcels or is there a way to structure a deal as to where I could sell off some of the land to repay the loan/investors and also retain a portion of it to develop with my own short term rentals.

This way, we receive continuous updates from attorneys who eat, sleep, and breathe lending at minimal cost and we know we are always up to date.

The money that you end up owing to repay the loan over the 5 year term is now post income tax money unlike how you traditionally are supplying your 401k with pre-tax money.  

Hard money loans typically have higher interest rates and shorter repayment terms than traditional mortgages.

Be sure to calculate the impact this might have on your ROI.Fees: Be prepared for additional fees, such as origination fees, appraisal fees, and possible prepayment penalties.Things to Consider:Loan Terms: Understand the interest rate, the loan term, and any repayment penalties.

If you transfer it into an LLC after securing the HELOC, your lender could invoke the due-on-sale clause, meaning they could demand full repayment of the loan immediately.