The HELOC would likely be more efficient for securing the acquisition as it would be considered 'cash.' 

But I also want to give him security of having a lien on a property that is not the subject property.

If the land is part of the security - then you'd need to refinance the debt most likely.

Consider all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.

The protections are there because beat cops are not qualified to determine who is a tenant and who is a criminal.Just as LL should not provide keys without rent, security deposit, credit check, etc, tenant should not pay a dime without a lease agreement that gives them certain rights.  

Security deposit is $2000.

In order to secure our FHA loan, we opted for a strategy known as "cash for keys," where we incentivized one set of tenants to vacate.

That being said, is it as easy as buying 5 to 10 $50k to $100k properties in Central USA, and securing a section 8 tenant?

@June Broce We do a ton of Transactional Lending for wholesalers looking to double close, some investors who are doing seller finance deals or same day purchase and refinance into a DSCR loan.If you can assign the deal and save yourself some money, it's the better option but I 100% understand why someone also prefers to double close and secure their profits depending on the scenario.With that said, you can buy/sell the land SAME day for a legit double closing. 

It is gated, secure, a larger resort, with hotels, restaurants, shops, scuba, snorkeling, a dolphin encounter, etc.It has a marina and golf course.