Understand house hacking you have roommates essentially.

 I am also looking at the HELOC as a 1st and use the principles proclaimed in the Replace Your Mortgage pitch which I understand to be, Use it as a checking account and putting all your income into the HELOC and then pay bills from that account thereby using all income to more quickly reduce the interest. 

If so, reach out to them and ask about the experience You have made a very interesting point on house hacking that I never thought about; have land with essentially another house on or beside it.

It's essential to evaluate each deal individually, considering factors like your specific market, property condition, and your own risk tolerance.Here's a quick summary of what you might do:70% Rule: Use this as your initial benchmark to assess deals, especially if you're looking at traditional financing with 70% LTV as a goal. 75% Rule: When you have access to lenders offering DSCR loans at 75% LTV, adjust your analysis to match this new lending option.

This is why having a SOLID plan in place is essential.401(k) - My partner utilized this for our initial round of funding.

Do not over-extend yourself and risk taking a large principle loss.With all of that said, a househack gives you more control than most other options.

If you split the equity in the future you will essentially be paying a higher price, as he would be entitled to the appreciation that has built over the time the agreement has been in place as well. 

When you price out the Principle interest taxes insurance and any HOA the rents in most states won't cover the payment unless you have BIG down payment or equity. 

Essentially taking out a second mortgage to pay for the property you mentioned.

You essentially robbing Peter to pay Paul.