some medical benefits of marijuana : -1.

You can do that with self-directed IRA, or better with truly self-directed Solo 401k plan, which has significantly higher contribution capacity (get the max tax break now), does not require a custodian and offers you checkbook control over your account (just some of the benefits). 

I have been looking for the right opportunity to come along, and a deal landed in my lap when another Realtor called me to provide a renovation estimate for a property which had essentially been a hoarder house.

It was my understanding that I will get a 250k deduction but that was essentially it other than investments I've made to my current home.

Your benefit is on a large cash on cash return, and equity through both appreciation and amortization (others paying your mortgage).  

Even though I say this about people, I'm one of them too, but it's by choice with me, because I need benefits for me and my son.

Will I be able to house hack and get all the tax benefits taking this approach?

If he gets injured while doing work for your benefit and you are "paying" him with rent discounts, are you liable for workman's comp?

Is this someone worth partnering up with since essentially the only thing he brings to the table is the funding part?

Would there be any benefit of putting it into an LLC, and all three of us paying rent into the LLC to rent the unit out.