If you're comfortable enough further extending your leverage, could you refi any of your duplexes and take some cash out? 

Harry Williams Depending on how aggressive spender you are, I would go for Amex Plum, they are amazing, the Deferred Pay option gives you 30 extended day pay time instead of your regular cycle cards, in short it adds another 30 days after your regular billing statement.

To extend the contract takes a simple fill in the blank addendum that anyone can do.

My partners happen to be family, and we have seen business misunderstanding in the extended family, and we want to avoid that at all cost. 

Thanks James Barnhart As an update I went to HD today to see if they had any open box or scratch stuff and the salesperson told me Black Friday sales start first week of November and run through Black Friday (and sometimes extended depending on sales).

I did park an extra car on the street for like a week or so and got an email to put it in the garage or driveway as we are not allowed to leave cars on the street overnight for extended periods of time. 

Since you’re already hosting, extending that to your unit can’t be that much more work, and you’re bound to get what you were collecting from the roommate in a fraction of the month.

I like Ryan's idea too with the 9 month lease maybe with an option to extend with mutual agreement if they can provide proof of employment and income prior to expiration of the lease.

A couple points from a first read of the details though it is far too early to tell:1) Extending the time period requirement for tax free gains on personal residence will hurt,2) There is some discussion of making edits to like-kind exchanges though it is not clear how that will work,3) The $500k mortgage deduction piece and property tax caps are individual tax provisions. 

Hi @Haley Mistler I don't see how you could do seller financing.For the buyer, seller financing is very similar to bank financing except that the seller (you) is now the lender.You could have done seller financing if you owned the house free and clear.But considering you have a mortgage on the house, you can't really extend a secured loan to your family collateralized on the house without paying off your lender.Ultimately, it seems like you really want to help your family member while no longer having that house as a liability.I am not sure if you have looked at it, but if I were you, I would check with a mortgage broker if there is any way they could get a loan in their own name.I imagine rates have gone down since you bought it, so they could have lower monthly repayment and if they really cannot afford the down payment.Assuming that they have always paid their rent on time for the past years that you have had them tenant, the main concern would be coming up with a down payment.Ultimately, I see great benefits in shifting your liabilties and getting rid of that property and sellling it to them.Considering that the amount owed on the house is what it is worth now, you would saved real estate commissions by selling it to them.Those savings could be used towards their down payment maybe?