I purchased the property off-market from my employer, Rapid Fire Investments (a regional wholesaling company).

Speaking of how "restrictive" home ownership is, that one is "stuck" to that location, can not engage in "todays" techno-world, restricting employability, restricting experience etc etc..

My concern is that a newer investor may risk their earnest money or may be on the hook on a deal (liquidiated damages up to 3% max on CAR RPA's) because they passed their contingencies or other while being lead to believe they could have qualified.Its like banking on a hail mary...As for FHA second use, the above sounds all woo woo and easy but I just did one of these recently and the underwriter wanted 25% equity on the vacating property (first FHA property) in order to qualify at "all," using one of the four exceptions for a 2nd FHA loan ( 1) larger family, 2)separation/divorce, 3) cosignor, 4) relocation because of employment).

I used to love getting a turkey every year from my employer, a few days before Thanksgiving. 

These commercial builders do tons of market research and since the city crane count is a  record high right now, that tells me that serious investors/large firms see a lot of potential in Chicago.4)Lastly,  employers are moving to the city to find younger talent: McDonald's, Walgreen's, Kraft-Heinz, Tyson-Hillshire, and ConAgra to name a few. 

If the revenue is of a business nature (not a passive nature), all profits are subject to 15.3% Self Employment Taxes in addition to Income Taxes.

hard money helps when you have a smoking deal and you want it get done fast (with that cash-like allure). however, like Jaron mentioned, it could be more expensive with fees, points, etc.

If you are in same line of work in self-employed business or with similar responsibility what you had before, lender can consider 1 year tax return.

Oshkosh truck is large corporation that makes vehicles for the military but this also leads to an up and down employments as they go from government contract to government contract.

If you are 1099, you do not have an employer, and you are not an employee.You are an independent contractor, and you have a client.