If he uses the HELOC responsibly, he'll be able to serially buy performing hard assets and eventually get to the point where the monthly cash flow will provide future down payments.6.

We have offered to allow her to pay a reduced rent for the first few months as well but I am worried that may create some sort of limit on how much we can raise the rent on her in the future.

Hire an attorney and proceed with the eviction.In the future, I recommend you don't accept "landlord references" from friends or family members.

I've consulted a few times over the years with planners and with the way I buy properties, my liquidity requirements, and my concerns about about how government overspending affects the future, makes me a poor candidate for IRAs and 401(k)s with the stifling regulations.   

I hope we can potentially do future business together!

This might be a question for our insurance broker/future attorney, but wouldn't the LLC be formed in Indiana since the rental property is located there (versus Illinois where we will be living)?

I'd also suggest self-managing your first property to maximize cash flow and learn by doing for any future investments.

This kind of thing happens and now would be a good time to negotiate and add to your agreement how it will be handled in future.

I also see your point about avoiding bargain basement properties, especially insofar as tax shielding is easier with an asset of a reasonable size.Your point about barriers to entry is also interesting, since I suppose those barriers can be geography (natural boundaries of mountains/water), but you're probably referring to that which impedes future construction?

Congratulations for thinking about your future.