@Matt Matyas To have an actionable plan that will work in your area, you'll need to speak with the Town/county board of health and/or a reputable septic installer/maintainer.

I always make sure I have some skin in the game.I think this is most definitely the way for you to go.

With HomePossible and FHA, you can use proposed net rental income from the smallest 3 units to help you qualify, as long as you will occupy one of the units as a primary residence. 

Hi @Ellie Narie,You are correct that if the average stay is less than 7 days it does not qualify as a rental activity, so it must be reported on Schedule C. 

We only show to people who have been completely qualified by our process, and that becomes a very small number.

@Mike Loy, As a realtor you qualify for a Solo 401k, which has many advantages over self-directed IRA, here are few:Contribute 10X more than into an IRA (up to $61,000 per year per participant)Access up to $50,000 from your retirement account tax-free and penalties-free at any time prior to retirement via participant loan featureExempt from UDFI tax on leveraged real estateInvest tax-free using Roth 401k sub-accountCheckbook control without use of an LLC Custodian is not required = no custodian, transaction or asset based feesYou can read it in more details here:https://www.biggerpockets.com/blogs/2810/21298-sol...The bottom line is that if you qualify for Solo 401k - it would be way better than an IRA.

A qualified agent should be able to get more info on the property and how to proceed. 

I come from a middle class background- education and paralegal work are the world that parents knew not board rooms, mergers and acquisitions, and securing millions and millions of dollars for projects.

Lastly, I have to wonder if the person on the other end is even qualified for such a task.

@Luke FernandezYour wife is not on board.