In my experience, if things don't improve after the cure or quit notices, things usually don't get any better.

They will usually want to close in 2 weeks or less. 

Usually, Trust works better if you want to protect your personal asset.

What concerns me is that we are nearing the end of selling/renting season, which usually comes to a screeching halt at the end of October.

@Callum SinclairThis is a month-old post, so I'm probably late.The simplest and most effective setup is usually to keep the whole business under your name or an LLC that is 100% owned by you, and set up your family members as lenders, as opposed to partners.If funding the deal makes it impossible, due say to your credit, then you can reverse: have your dad own the property under his name or his LLC, and set yourself up as a contractor for him.Bottom line: it is case by case.

When I get them it's awesome because they're usually one guest per room and barely add wear and tear on the home. 

It usually happens only when the buyer or seller call the bank and ask the bank for their blessings, Not a smart thing to do IMHO and it's unnecessary to contact the bank. 

Without having to go to the Bank and getting Owner Financing would be a way to get a low down payment or having to get  "House Hacking" insured loan and having to live there for usually about 12 months.Showing the Owner on paper how that kind of loan how much more he could make and how spreading out their income could reduce their tax liability. 

I am housing hacking and using my VA loan and from what I have heard the VA is usually very strict with the inspections. 

Ya you'll find that a lot of lawyers and other professionals will be clueless on real estate.All you need is 1) A rental agreement - you can find these usually pre-made in your city.