As you said, have them pay for the oil and i would have a " security deposit" of a full tank of oil added. just remember, they don't fill the tank and there is no heat in the house during the winter, guess what happens to your pipes and your house ?

This leave you at $2,000-10,000 dollar profit which is still good but charge a upfront deposit of $2,000 and get $2,000 on the back end at the closing table that is $4,000 dollar profit plus a easy flip to the buyer. 

Background check of tenantRent RollUtilities detailLast 3 years tax returnSecurity deposit of tenantProperty managementrecent improvement/maintenance recordWhat are some creative ways to structure this deal without completely liquidating my capital?

Did you take a pet deposit for the cats?

Since it's in Chicago you might wanna avoid security deposits and opt instead for a non-refundable move in fee

Even if you can recover refinishing costs from a tenant's deposits you're shortening the life of the floor, which is expensive to replace.If you put carpet or some other flooring down they'll be preserved until you do decide to sell.

Unfortunately, this is why you should at least get a sizable, non-refundable deposit with the signing of the assignment agreement.  

No inspection contingency and a 10% earnest money deposit.

(Giving them a reason to pay a premium rent.)Lease Purchase Example- $100K Home w/ 10% down.Assuming they are looking for an FHA, I'd like to take a 3.5% deposit up front.

David Stone unless you have a huge deposit saved up, banks are unlikely to approve a mortgage that size on a $22k/yr income.I say take the owner financing even if it is 3-4% higher than bank rate.