Now i'm married, have three kids and a wife that want me to retire.I'm usually the jack-of-all-trades and Do-it-all-by-myself guy, but in order to advance at a more rapid pace, it helps to have a support group. 

well assuming it meets the QM rules for owner occ.. etc.the scenario you presented is not a very attractive note unless the discount was HUGEPV is what investor look at.... what rate of return they want and in notes its usually 8 to 12% APR but with 100% leverage most investors will only pay on face value about 60 to 70% LTV ... so right off the top you would be taking a substantial hair cut.No secret what your trying to do.. but I surmise you will very quickly realize its not realistic .. the discount would be such that it makes it a no go.If your thinking someone will lock up their money for 10 years at 5% well thats not going to happen especially at 100% LTV... 

'As long as you have a W2 job and you can prove the deal is self supporting through the sale transition and any repositioning that I intend to do, then we (the bank) will loan you money all day!'  

Anyways I appreciate all advice/support/criticism.

Maybe make some cosmetic updates and list is for rent closer to 600-800 if you think the market will support it.

Any special rules for landlords in winter time in Chicago, Cook County, Illinois like ashing walkways or puting salt on those?

If we use the 50% rule, that makes cash flow 7800 per year and that makes cash-on-cash 8.76%.  

Then, You are taking the Risk that the bottom Support in the Market, Stock or Real Estate, will hold out.

@Himanshu JainIt all depends on how aggressive the board is with rentals and it sounds like this Association sticks to the rules. 

It doesn't quite meet the 50% rule but I'm paying it off in 15 years instead of 30 and I could always re-fi or get a HELOC to get some of my cash out if a major expense like a roof or something popped up.