This new tax increases the cost of tourism and will, overall, raise the short-term rental rates in our city.Additionally, keep in mind that you already pay the mill levy annually on your residential property as well as reporting any rental income on your state and federal tax return.

If you are getting a quality tenant in that area and you already have instant equity the long term return of holding it would most likely be the best verses selling it as a flip.

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?

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

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.