Do you have a deposit from him, and if so, are you intending to return it back or keep it.

What kind of renturn or cash flow should I expect when using 100% financingWhat kind of return or cash flow should I expect when using 100% financing?

I appreciate the tangible value (of real estate... people will always need a place to live) vs the volatile value of a stock on paper that may not be worth the ink its written in or too easily misrepresented or manipulated.

Seller financing keeps your return of principal very low each year not bumping you up to higher tax brackets... 

My point is that if I can keep tenants happy - relatively easily and cheaply - I'd probably just do it ... on a case by case basis of course ... and my decision would depend a lot on those three aforementioned points.

Tax payer is going to be defined as the entity filing the tax return that reports all of the activity of the real estate. 

This would quickly return most of my cash to me, which I need in order to complete a fairly extensive renovation prior to moving in.The problem I'm running into with my current lender is the timing. 

What are some ways to structure an agreement where I can retain and rent the property but he can get a good return as well?

That lead me to looking for below market, distressed single units, in Chicago, in neighborhoods with a high rent demand, and that still seems like a decent idea but I'm not getting the return I'd like, but would still be netting positive.

You have aggressively dropped down your student debt, I say continue the progress and pay it off for you can potentially buy a bigger home (4 fam) owner occupied once you are done.Or if you are comfortable with debt you can make a bigger return investing and that can help you pay down your debt. if you are I will get a owner occupied 2-4 family with a seller concession (depending how competitive your area is) for you won't have a high closing cost.